A general enantioselective route to the chamigrene natural product family
KAUST Grant NumberKUS-11-006-02
Permanent link to this recordhttp://hdl.handle.net/10754/597276
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AbstractDescribed in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and α-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented.
CitationWhite DE, Stewart IC, Seashore-Ludlow BA, Grubbs RH, Stoltz BM (2010) A general enantioselective route to the chamigrene natural product family. Tetrahedron 66: 4668–4686. Available: http://dx.doi.org/10.1016/j.tet.2010.04.128.
SponsorsThis publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank the NIH-NIGMS (R01 GM080269-01, postdoctoral fellowships to D.E.W. and I.C.S.), Abbott, Amgen, Bristol-Myers Squibb, Merck, and Caltech for generous funding; Materia, Inc. for their kind donation of catalyst 49 used in these studies; Professors Mercedes Cueto and Karen L. Erickson for their kind donation of natural samples of elatol (1); Professor Adusumilli Srikrishna for copies of <SUP>1</SUP>H and <SUP>13</SUP>C NMR spectra of synthetic (+/-)-laurencenone C ((+/-)-8) and (+/-)-alpha-chamigrene ((+/-)-5): and Professor Peter B. Dervan and David M. Chenoweth for use of their HPLC. Finally, B.M.S. thanks all of his current and former co-workers and colleagues who have made working at Caltech over the past 10 years such an enjoyable experience. As evidenced by the collaborative nature of this project, the spectacular environment at Caltech is one-of-a-kind and second-to-none.
PubMed Central IDPMC2925317
CollectionsPublications Acknowledging KAUST Support
- The catalytic asymmetric total synthesis of elatol.
- Authors: White DE, Stewart IC, Grubbs RH, Stoltz BM
- Issue date: 2008 Jan 23
- Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles.
- Authors: Cao ZY, Zhou F, Zhou J
- Issue date: 2018 Jun 19
- Design and stereoselective preparation of a new class of chiral olefin metathesis catalysts and application to enantioselective synthesis of quebrachamine: catalyst development inspired by natural product synthesis.
- Authors: Sattely ES, Meek SJ, Malcolmson SJ, Schrock RR, Hoveyda AH
- Issue date: 2009 Jan 28
- Synthesis of spirocyclic thiazolidinediones using ring-closing metathesis and one-pot sequential ring-closing/cross metathesis.
- Authors: Dhara K, Paladhi S, Midya GC, Dash J
- Issue date: 2011 May 21
- Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ<sup>6</sup> -α-Iodoketone.
- Authors: Trajkovic M, Ferjancic Z, Saicic RN, Bihelovic F
- Issue date: 2019 Mar 21