A general enantioselective route to the chamigrene natural product family

Handle URI:
http://hdl.handle.net/10754/597276
Title:
A general enantioselective route to the chamigrene natural product family
Authors:
White, David E.; Stewart, Ian C.; Seashore-Ludlow, Brinton A.; Grubbs, Robert H.; Stoltz, Brian M.
Abstract:
Described 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.
Citation:
White 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.
Publisher:
Elsevier BV
Journal:
Tetrahedron
KAUST Grant Number:
KUS-11-006-02
Issue Date:
Jun-2010
DOI:
10.1016/j.tet.2010.04.128
PubMed ID:
20798895
PubMed Central ID:
PMC2925317
Type:
Article
ISSN:
0040-4020
Sponsors:
This 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.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorWhite, David E.en
dc.contributor.authorStewart, Ian C.en
dc.contributor.authorSeashore-Ludlow, Brinton A.en
dc.contributor.authorGrubbs, Robert H.en
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-25T12:29:37Zen
dc.date.available2016-02-25T12:29:37Zen
dc.date.issued2010-06en
dc.identifier.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.en
dc.identifier.issn0040-4020en
dc.identifier.pmid20798895en
dc.identifier.doi10.1016/j.tet.2010.04.128en
dc.identifier.urihttp://hdl.handle.net/10754/597276en
dc.description.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.en
dc.description.sponsorshipThis 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.en
dc.publisherElsevier BVen
dc.titleA general enantioselective route to the chamigrene natural product familyen
dc.typeArticleen
dc.identifier.journalTetrahedronen
dc.identifier.pmcidPMC2925317en
dc.contributor.institutionDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125.en
kaust.grant.numberKUS-11-006-02en
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