Tet. Lett. Is other people
Stereoselective Total Synthesis of Hainanolidol and Harringtonolide via Oxidopyrylium-Based [5 + 2] Cycloaddition
Weiping Tang et al., J. Am. Chem. Soc., 2013, ASAP; [] [] []
Everyone who's studies organic chemistry long enough has a favorite reaction or two, although unusually in my case I’ve never actually performed either of mine. One is the
last year for Carmen’s, first discovered by Bryce-Smith (in Reading, UK, of all places) and sharpened into a useful synthetic tool by Wender,
and others. The second is probably the [5 + 2] oxidopyrylium cycloaddition, a handy way of making 7-membered rings with nary a metal in sight.[1] Neither is particularly common in total synthesis, so imagine my delight when I saw the latter featured in Tang’s recent synthesis of harringtonolide a couple of weeks back.
The target in question comes from the Cephalotaxus genus of plants, which—by means of the
cephalotaxine and harringtonine alkaloids—has provided synthetic chemists with a great deal of entertainment over the past 50 years or so. It’s interesting to note that the Cephalotaxus genus itself belongs to the larger family Taxaceae, which also encompasses the yew tree Taxus baccata, well known to natural products chemists as the original source of the famous microtubule stabiliser and anti-cancer drug taxol. Well, it seems that humankind has again struck gold in the Taxaeae family as harringtonolide has recently been demonstrated to be a remarkable potent and selective anti-neoplastic agent. But enough on taxol and taxonomy—let’s talk synthesis!
The group’s plan relied on the use of the aforementioned [5 + 2] oxidopyrylium cycloaddition to construct the seven membered ring. This clever, central disconnection essentially reduces the rather intimidating carbon skeleton of harringtonolide to a comparatively simple problem in decalin synthesis and—although it's a rather strange looking species—the precursor to the oxidopyrylium required to pull it off is just a simple furan.
The route began with the bicyclic enone shown below, and it probably won’t surprise anyone to learn that this was synthesised using the famous Robinson annulation, although at first glance it does seem a little odd that the racemic form of this building block was used, given that this reaction is usually easily rendered enantioselective with a little organocatalysis.[2] However, on closer inspection it turns out that—although no comment is made in the paper itself—if one delves into the SI the group does detail their unsuccessful search for a suitable catalyst for in total synthesis even 'general' reactions are often far from universal!
Pushing on with the racemic route, the enone was γ-hydroxylated in a vinylogous Rubottom-type oxidation involving diene formation, followed by treatment with oxone. A 4:1 mixture of diastereomers
was obtained (favouring the unwanted epimer!), and this mixture was carried though the next four steps. A second Rubottom-type
reaction—involving silyl enol ether formation, followed by treatment with osmium tetroxide—was then used to α-hydroxylate the other side of the ketone.[3] Having served its purpose of activating the nearby methylene groups for oxidation, the ketone was now reduced to give the trans-diol, which was then protected as the bis(TBS ether).[4] Now, with the conformational preference of the ring system sufficiently altered by these events, the incorrectly set stereocentre from the first oxidiation could finally be epimerized. Thus, deprotection, oxidation and reduction gave the alcohol allyic alcohol with better than 20:1 diastereoselectivity in favour of the desired compound, and this stereochemical information was now transferred to the righthand ring by means of a of a Claisen rearrangement. This was performed by the now-justifiably-uncommon method of mercury trifluoroacetate-catalysed vinyl transfer, followed by heating the vinyl ether obtained in refluxing toluene. The resulting aldehyde was then converted to the corresponding Weinreb amide in order to allow installation of the furan ring at a later stage, and finally an allylic oxidation was carried out to give the enone shown below.
Although the introduction of a carbonyl group into the left-hand ring may seem counterintuitive (as no oxygenation is ultimately required in this half of the bicycle), it was hoped that its presence would facilitate formation of the thermodynamically unfavourable cis-decalin. It was anticipated—correctly—by the group that reduction of this carbonyl—or its hydrazone—would occur via hydride delivery to the top face of the molecule and they exploited this reactivity to generate an diazene intermediate that underwent [3,3]-sigmatropic rearrangement set the remaining ring junction stereocentre with the required stereochemistry.[5] Next, the furan was introduced by addition of 2-furylmagnesium bromide to the Weinreb amide, and it was now time to test the key [5 + 2] cycloaddition. First, oxidative expansion of the furan h this was achieved by reduction of the adjacent ketone to the secondary alcohol, which was then used to direct Achmatowicz oxidation of the furan itself with tert-butylhydroperoxide and a vanadium catalyst. The oxidation and rearrangement produced the expected hydroxypyranone in good yield, and this was then acetylated with acetic anhydride in pyridine. Finally, heating this somewhat unstable intermediate with DBU in refluxing chloroform lead to oxidopyrylium formation (via elimination of acetic acid and tautomerisation) and the anticipated cycloadduct was isolated in excellent yield.[6]
Now that the key step had successfully been realised, the group faced the task of converting the oxabicyclooctane ring fromed by the [5 + 2]-cycloaddition into the tropone ring found in the natural product.[7] First, the additional methyl group required was introduced by simple addition of methyl magnesium bromide to the enone under substrate control. This was then followed by selective removal of one of the TBS groups using trichloroacetic acid, and lactonisation. Now—at least according to the group’s initial plan—only a coup a Dauben reaction was used to oxidatively transpose the newly formed tertiary allylic alcohol to the enone and conditions were now investigated for the removal of the unwanted oxygen bridge. Unfortunately, no direct way of dehydrating the oxabicyclooctane directly to the tropone could be found, and a new endgame had to be devised to sidestep this problem.
Going back a step, the tertiary alcohol that had been oxidised in the previous attempt was instead treated with thiophenol and boron trifluoride etherate, resulting in SN2’ displacement to give the allyl thioether. Removal of the sulfide α-proton using LDA in THF/HMPA then resulted in cleavage of the ether bridge by elimination. Surprisingly, only one of the two possible isometric dienes—the desired one—was
formed, and in excellent yield – the route was back on track!
Having served its purpose, the thioether was now removed over a three step sequence involving protection of the vicinal alcohol, oxidation to the sulfoxide and reductive removal by C–S cleavage with samarium diiodide (pepped up with a little DMPU/MeOH). Introduction of the tropone oxygen was then carried out by [4 + 2] cycloaddition of the cycloheptadiene with singlet oxygen, followed by a DBU mediated Kornblum–DeLaMare rearrangement to the enone.[8] Finally, treatment with p-TSA cleaved the TES group and effect a double dehydration to form the much sought after tropone to give the alcohol in good yield. It turns out that this penultimate compound is actually a natural product in its own right and—as its (biomimetic) conversion
to harringtonolide had already been demonstrated in the lab—the group had now achieved the formal total synthesis of their target. However—with barely enough material in hand—they still attempted to perform the final reaction themselves, eventually producing 0.2 mg of the target!
Although its length, linear nature and low overall yield do detract a little, and the final path traveled was somewhat circuitous, I—for one—enjoyed the journey. Well done guys!
There was a dedicated review on this reaction in Tetrahedron a few years back (). A more general review on the [5 + 2] reaction was published by Jeffery Stryker at the start of this year, covering the full gamut of metal catalysed versions as well ().
In fact, the
used to prepare such substrates is generally regarded as the seminal example of useful asymmetric organocatalysis in the literature. There are many, many reports of this type of cascade in asymmetric decalone synthesis, and of course the reaction is used to make the famous , which has been the starting point for countless (well, several) total syntheses. If I wanted to point out another link to taxol, I could tell you that Danishefsky used the Wieland–Miescher ketone as the starting point for his epic total synthesis.
The DABCO’s just there to accelerate the reaction’s pretty slow without ligands on the osmium – just ask Barry Sharpless. Quinuclidine also does this job well.
Curiously, when this reaction was performed with sodium triacetoxyborohydride—a reagent that normally gives trans-diols by intramolecular delivery of hydride—only the cis-diol was obtained (as evidenced by its conversion to the corresponding acetonide. Fortunately, sodium borohydride displayed excellent selectivity for the required trans-diol.
A variant of this trick has been recently used by
Obviously in this synthesis this step is not biomimetic, but there are a few cases where this reaction is thought to occur in Nature. The most interesting one that I can think of right now is in the biosynthesis of the natural product intricarene, whose name is cognate with the English word ‘intricate’, thanks to that tortuous structure. The proposed cycloaddition links it to a cembranoid co-isolate, bipinatin J, and has successfully been mimicked in the lab by the groups of Pattenden and Trauner.
Scheme 1 from Trauner’s synthesis ()
7. Although tropone is probably one of the first aromatic carbocyclic compounds that everyone thinks of after benzene (well, apart from maybe ) it wasn’t until Dewar’s work in 1945 that it occurred to anyone that aromatic rings can come in all shapes and sizes. Dewar was very interested in ‘non-standard’ aromatic compounds, and
is named for him, as I .
8. When was the last time you saw one of those so late in a big total synthesis? I'm thinking Nicolaou's 2011 route to epicoccin G (), although I dimly recall one in a taxol synthesis... maybe Kuwajima's?
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Sorry, your blog cannot share posts by email.硫原子转移反应及其药物与天然产物合成应用--《中国化学会第29届学术年会摘要集——第07分会：有机化学》2014年
硫原子转移反应及其药物与天然产物合成应用
【摘要】：Sp3 C-I键活化一直是钯催化领域的难点之一,尤其是含β-H的sp3 C-I键体系,因为相应的烷基钯中间体容易发生β-H消除。以该体系为依托,1)实现了钯催化条件下非活化烷基碘原子转移环化反应1;2)实现了钯催化的无金属还原剂的sp2、sp3 C-I键的还原偶联反应2;3)实现了以Na2S2O3作为硫源的钯催化分子内双C-S键构建的偶联反应3。于此发现基础上,初步建立了绿色化无恶臭硫化试剂的开发,1)实现了一系列芳基官能化合物的分子间双C-S键构建反应研究4;2)运用亚磺酸钠参与此类硫原子转移反应研究中,成功实现了挑战性非对称过硫化合物结构的构建5,此类S-S键构建方法可用于Epicoccin A、C、D等具备重要生理活性复杂天然产物的合成研究中。在此过程中发现了氧化C-C键活化的特殊机理6。
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【分类号】：O621.25【正文快照】：
硫原子转移反应及其药物与天然产物合成应用@姜雪峰$华东师范大学!上海市中山北路Sp3 C-I键活化一直是钯催化领域的难点之一,尤其是含β-H的sp3 C-I键体系,因为相应的烷基钯中间体容易发生β-H消除。以该体系为依托,1)实现了钯催化条件下非活化烷基碘原子转移环化
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BrownNSF AGEP Postdoctoral Research Fellow, Department of Chemical Engineering, University of Michigan03/17/20113:00 pmPaul Helquist, PhDProfessor, Department of Chemistry and Biochemistry, University of Notre Dame03/04/20113:00 pmDr. Vera SamburovaAssistant Research Professor, Division of Atmospheric Sciences, Desert Research Institute02/25/20113:00 pmDr. Yanhu Wei Research Associate, Northwestern University, Dept. of Chemical & Biological Engineering02/24/20114:00 pmDr. Shuangbing HanPostdoctoral Fellow, Northwestern University, Dept. of Chemical & Biological Engineering DOE's Non-Equilibrium Energy Research Center02/22/201110:00 amMr. Linsheng FengDoctoral Candidate, Department of Chemistry, Michigan Technological University02/18/20113:00 pmDr. Tim RoyappaAssociate Professor, Department of Chemistry, University of West Florida02/15/20113:00 pmMs. Nina TyminskaDoctoral Student, Department of Chemistry, Michigan Technological University02/04/20113:00 pmMichigan Technological University EITDean of Students Office01/28/20113:00 pmDr. Caryn HeldtAssistant Professor, Department of Chemical Engineering, Michigan Technological University01/20/20111:00 pmDr. Bingyun SunResearch Scientist, Institute for Systems Biology, Seattle, Washington12/8/20103:00 pmDr. Fabien GoulayUniversity of California, Berkeley12/6/20103:00 pmDr. Song GuoUniversity of Texas at Austin11/29/20103:00 pmDr. Heather AbbottGeorgia Institute of Technology, School of Chemistry & Biochemistry11/22/201010:00 amMs. Colina DuttaMS Candidate, Department of Chemistry, Michigan Technological University11/12/20103:00 pmDr. Reza Shahbazian YassarAssistant Professor, Mechanical Engineering - Engineering Mechanics, Michigan Technological University11/05/20103:00 pmDr. Adrienne MinerickAssociate Professor, Department of Chemical Engineering, Michigan Technological University10/12/20109:00 amMs. Mimi YangDoctoral student, Department of Chemistry, Michigan Technological University10/01/20103:00 pmJohn S. Maass and Rudy L. LuckAssociate Professor, Department of Chemistry, Michigan Technological University09/24/20103:00 pmDr. Frank KeutschAssistant Professor, Department of Chemistry, University of Wisconsin-Madison09/17/20103:00 pmDr. Soheir Tawfik&09/16/20104:00 pmDr. Robert BatesUniversity of Florida08/27/20109:00 amSingaravelu VelayudhamDoctoral Candidate, Department of Chemistry, Michigan Technological University08/05/20103:00 pmNa HuDoctoral Student, Department of Chemistry, Michigan Technological University04/27/20103:00 pmMs. Rajni KalavendiMS Candidate, Department of Chemistry, Michigan Technological University04/23/20103:00 pmDr. Masha V. PetrovaFounder and CEO of MVP Modeling Solutions, LLC in Hockessin, DE04/23/20101:00 pmMr. Steven JohnsonPhD Candidate, Department of Chemistry, Michigan Technological University04/16/20103:00 pmDr. Petar R. DvornicSenior Research Scientist and Professor of Polymer Chemistry, Michigan Molecular Institute04/16/20109:00 amNing ChenDoctoral student, Department of Chemistry , Michigan Technological University04/09/20103:00 pmDr. Karol KowalskiSenior Research Scientist, WR Wiley Environmental Molecular Sciences Laboratory, High Performance Software Development, Pacific Northwest National Laboratory04/06/20102:30 pmMs. Soumyashree SreehariDoctoral candidate, Department of Chemistry, Michigan Technological University04/02/20103:00 pmDr. Peter BealProfessor, Department of Chemistry, UC Davis03/30/20103:00 pmDr. Tarun K. DamDepartment of Molecular Pharmacology, Albert Einstein College of Medicine03/19/20103:00 pmDavid Bezotte, JR Van Pelt and Opie LibraryReference and Instruction Librarian03/05/20103:00 pmDr. Eva ZurekAssistant Professor, Department of Chemistry, State University of New York at Buffalo03/03/20103:00 pmDr. Haibo YuPostdoctoral Scholar, Beno顃 Roux's Lab, Department of Biochemistry and Molecular Biology, The University of Chicago02/26/20103:00 pmDr. Ching-An Peng, Professor,
James and Lorna Mack Endowed Chair in BioengineeringDepartment of Chemical Engineering, Michigan Technological University02/19/20103:00 pmDr. Amy MarcarelliAssistant Professor, Department of Biological Sciences, Michigan Technological University02/12/20103:00 pmDr. Wan Jin JahngAssistant Professor, Department of Biological Sciences, Michigan Technological University01/15/20103:00 pmPeter F Method, PhDAssociate Director Indiana State Department of Toxicology (retired)12/04/20093:00 pmDr. Sylvie Garneau-TsodikovaJohn G. Searle Assistant Professor of Medicinal Chemistry, College of Pharmacy, Research Assistant Professor, LSI, University of Michigan, Life Sciences Institute 11/13/20093:00 pmDr. Paul DoskeyProfessor, Civil and Environmental Engineering and Forest Resources and Environmental Science, Michigan Technological University11/06/20093:00 pmDr. Carol HirschmuglProfessor, Department of Physics, University of Wisconsin, Milwaukee10/30/20093:00 pmDr. Rose CoryAssistant Professor, Environmental Sciences and Engineering, University of North Carolina at Chapel Hill, Gillings School of Global Public Health10/23/20093:00 pmDr. Charles Brooks IIIUniversity of Michigan10/16/20093:00 pmProf. Dr. Dr.h.c. N. R鰏chTechnische Universit鋞 M黱chen, Department Chemie, Theoretische Chemie 10/02/20093:00 pmDr. Shiyue FangAssistant Professor, Department of Chemistry, Michigan Technological University09/25/20093:00 pmDr. Michael GibsonProfessor and Chair, Department of Biological Sciences, Michigan Technological University09/18/20093:00 pmDr. Ming Ming ZhouDr. Harold and Golden Lamport Professor and Chairman Department of Structural and Chemical Biology, Mount Sinai School of Medicine07/10/200910:00 amMartha J Barajas MenesesDoctoral Student04/17/20094:00 pmLarry MaillouxMS Defense04/17/20093:00 pmMark SchoenfischAssociate Professor, Department of Chemistry, UNC Chapel Hill04/06/20094:00 pmDr. Lynn MazzoleniAssistant Professor, Department of Chemistry, Michigan Technological University04/06/20093:00 pmDr. Donald DaavettilaEmeritus Faculty, Department of Physics04/03/20093:00 pmDr. Wei YangAssistant Professor, Department of Chemistry & Biochemistry03/27/20093:00 pmDr. Rani JosephCochin University of Science and Technology03/20/20093:00 pmDr. Suvobrata ChakravartyMount Sinai School of Medicine02/20/20093:00 pmDr. Jin ChenMemorial Sloan-Kettering Cancer Center02/16/20093:00 pmDr. Benjamin DibleUniversity of Rochester02/10/20094:00 pmDr. Marcin PtaszekNorth Carolina State University01/23/20093:00 pmDr. Martin ThompsonAssistant Professor, Department of Chemistry, Michigan Technological University12/12/20083:00 pmD. Eric Walters, Ph.D.Professor, Dept. of Biochemistry & Molecular Biology, Rosalind Franklin University of Medicine and Science12/5/20083:00 pmJames R. Kincaid, PhDPfletschinger Habermann Professor, Department of Chemistry, Marquette University 11/21/20087:00 pm&&11/14/20083:00 pmMark Distefano, PhDAssociate Professor, Department of Chemistry, University of Minnesota11/12/20087:00 pmDr. William F. CarrollVice President for Chlorovinyl Issues at OxyChem and Adjunct Professor of Chemistry at Indiana University, Bloomington11/07/20083:00 pmDr. Yinan YuanPostdoctoral Research Associate10/24/20083:00 pmAndrew Feig, PhDAssociate Professor, Department of Chemistry, Wayne State University09/19/20083:00 pmDr. David ChesneyAssociate Professor, Safety Officer, Department of Chemistry, Michigan Technological University09/15/20087:00 pmDr. Al HazariUniversity of Tennesee09/12/20083:00 pmDr. Pushpa MurthyChair, Graduate Programs Committee, Department of Chemistry06/16/20083:00 pmLynn R. Mazzoleni, PhDPostdoctoral Research Associate, Earth and Environmental Sciences Division, Los Alamos National Laboratory, Los Alamos, New Mexico04/16/20083:00 pmDr. Caren L. Freel MeyersAssistant Professor, Johns Hopkins University School of Medicine, Department of Pharmacology and Molecular Sciences03/27/20084:00 pmDr. Piotr PiecuchUniversity Distinguished Professor, Department of Chemistry, Michigan State University03/07/20087:00 pm&&02/29/20087:00 pm&&02/22/20083:00 pmDr. Mark N. KobrakAssociate Professor, Department of Chemistry, Brooklyn College of the City University of New York 02/15/20083:00 pmDr. Michelle KnowlesPostdoctoral Fellow, Vollum Institute, Oregon Health & Science University02/08/20087:00 pm&&02/01/20083:00 pmDr. Dar韔 J. StacchiolaChemistry Department, Brookhaven National Laboratory01/25/20083:00 pmDr. Megan C. FrostAssistant Professor, Department of Biomedical Engineering, Michigan Technological University12/14/20077:00 pm&&12/07/20073:00 pmDr. Haiying LiuAssistant Professor, Department of Chemistry, Michigan Technological University11/30/20073:00 pmDr. Debra D. CharlesworthAssistant to the Dean, Graduate School, Michigan Technological University11/23/20077:00 pm&&11/16/20077:00 pm&&11/09/20073:00 pmDr. Eugenijus UrneziusAssistant Professor, Department of Chemistry, Michigan Technological University10/26/20073:00 pmDr. Chae S. YiAssociate Professor, Department of Chemistry, Marquette University10/19/20073:00 pmDr. Zhongwu GuoProfessor, Department of Chemistry, Wayne State University10/12/20073:00 pmDr. Lesley Lovett-DoustProvost and Vice President for Academic Affairs10/05/20073:00 pmElizabeth C. Minor, PhDAssoc. Prof., Large Lakes Observatory and Dept. of Chem. & Biochem., Univ. of Minnesota, Duluth09/28/20073:00 pmDr. Michael VanNieuwenhze Associate Professor, Department of Chemistry, Indiana University09/21/20073:00 pmDr. David ChesneyAssociate Professor, Safety Officer, Department of Chemistry, Michigan Technological University09/14/20073:00 pmPatricia A. Gotschalk, J.D.Director of Student Judicial Affairs, Michigan Technological University09/07/20073:00 pm&K-Day桸o seminar&02/02/20073:00 pmB.A. Howell Center for Applications in Polymer Science - Central Michigan University12/15/20064:00 pmDr. Anja MeullerAssistant Professor of Chemistry - Central Michigan12/08/20063:00 pmDr. Peter AndreannaAssistant Professor - Wayne State12/01/20063:00 pmDr. Eugene UrneziusAssistant Professor - Michigan Technological University11/10/20063:00 pmDr. Keith WooProfessor and Associate Chair - Iowa State11/03/063:00 pmDr. Joan KleypasISSE Scientist - University of Colorado10/27/20063:00 pmDr. Adrian MichaelAssociate Professor Electrochemistry/Bioanalytical Chemistry - University of Pittsburgh10/20/20063:00 pmDr. Jason GestwickiResearch Assistant Professor - U Michigan10/06/20063:00 pmDr. Peter PolitzerProfessor of Chemistry - UNO5/8/20064:00 pmDr. Yorke E. RhodesNew York University4/7/20063:00 pmDr. Haiying LiuAssistant Professor - Department of Chemistry Michigan Technological University3/31/20063:00 pmDr. Chung-Jui TsaiAssociate Professor - School of Forest Resources and Environmental Science Michigan Technological University3/24/20063:00 pmDr. Amy R. HowellProfessor - Department of Chemistry, University of Connecticut3/17/20063:00 pmDr. Dehua PeiProfessor, Department of Chemistry - The Ohio State University2/17/20063:00 pmDr. Kristopher McNeillMcKnight Land-Grant Assistant professor, Department of Chemistry University of Minnesota11/11/20053:00 pmDr. Venjatram R. MereddyAssistant Professor - Dept. of Chemistry and Biochemistry, University of Minnesota Duluth10/10/20053:00 pmNicholas A. KotovAssociate Professor - Department of Chemical Engineering, University of Michigan9/23/20053:00 pmDr. Mark SpallerAssistant Professor - Department of Chemistry, Wayne State University9/16/20053:00 pmDr. Mary Kay PflumAssistant Professor - Department of Chemistry, Wayne State University
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