Handle URI:
http://hdl.handle.net/10754/600040
Title:
Total Syntheses of Cyanthiwigins B, F, and G
Authors:
Enquist, John A.; Virgil, Scott C.; Stoltz, Brian M.
Abstract:
A concise and versatile approach toward the preparation of the cyanthiwigin family of cyathane natural products is described. By leveraging a unique double asymmetric catalytic alkylation procedure it is possible to quickly establish two of the most critical stereocenters of the cyanthiwigin framework with high levels of selectivity and expediency. The synthetic route additionally employs both a tandem ring-closing cross-metathesis reaction, and an aldehyde-olefin radical cyclization process, in order to rapidly arrive at the tricyclic cyathane core of the cyanthiwigin molecules. From this unifying intermediate, the preparations of cyanthiwigins B, F, and G are attained swiftly and without the need for protecting groups.
Citation:
Enquist JA, Virgil SC, Stoltz BM (2011) Total Syntheses of Cyanthiwigins B, F, and G. Chem Eur J 17: 9957–9969. Available: http://dx.doi.org/10.1002/chem.201100425.
Publisher:
Wiley-Blackwell
Journal:
Chemistry - A European Journal
KAUST Grant Number:
KUS-11-006-02
Issue Date:
18-Jul-2011
DOI:
10.1002/chem.201100425
PubMed ID:
21769952
PubMed Central ID:
PMC3365662
Type:
Article
ISSN:
0947-6539
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). The authors wish to thank NIH-NIGMS (R01M080269-01), Amgen, Abbott, Boehringer Ingelheim, Merck, and Bristol-Myers Squibbs, GlaxoSmithKline, Johnson and Johnson, Amgen, Merck Research Laboratories, Pfizer, Novartis, Roche, Abbott Laboratories, Boehringer-Ingelheim, AstraZeneca, and Caltech for financial support. We also wish to thank Dr. M. W. Day and Mr. L. M. Henling for X-ray crystallographic expertise, Dr. Andrew Harned, Dr. David White, Daniel Caspi, and J. T. Mohr for helpful discussions, and Professor Mark T. Hamann for authentic samples and spectra of cyanthiwigins B, F, and G. Ruthenium olefin metathesis catalysts were generously donated by Materia.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorEnquist, John A.en
dc.contributor.authorVirgil, Scott C.en
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-28T06:34:52Zen
dc.date.available2016-02-28T06:34:52Zen
dc.date.issued2011-07-18en
dc.identifier.citationEnquist JA, Virgil SC, Stoltz BM (2011) Total Syntheses of Cyanthiwigins B, F, and G. Chem Eur J 17: 9957–9969. Available: http://dx.doi.org/10.1002/chem.201100425.en
dc.identifier.issn0947-6539en
dc.identifier.pmid21769952en
dc.identifier.doi10.1002/chem.201100425en
dc.identifier.urihttp://hdl.handle.net/10754/600040en
dc.description.abstractA concise and versatile approach toward the preparation of the cyanthiwigin family of cyathane natural products is described. By leveraging a unique double asymmetric catalytic alkylation procedure it is possible to quickly establish two of the most critical stereocenters of the cyanthiwigin framework with high levels of selectivity and expediency. The synthetic route additionally employs both a tandem ring-closing cross-metathesis reaction, and an aldehyde-olefin radical cyclization process, in order to rapidly arrive at the tricyclic cyathane core of the cyanthiwigin molecules. From this unifying intermediate, the preparations of cyanthiwigins B, F, and G are attained swiftly and without the need for protecting groups.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). The authors wish to thank NIH-NIGMS (R01M080269-01), Amgen, Abbott, Boehringer Ingelheim, Merck, and Bristol-Myers Squibbs, GlaxoSmithKline, Johnson and Johnson, Amgen, Merck Research Laboratories, Pfizer, Novartis, Roche, Abbott Laboratories, Boehringer-Ingelheim, AstraZeneca, and Caltech for financial support. We also wish to thank Dr. M. W. Day and Mr. L. M. Henling for X-ray crystallographic expertise, Dr. Andrew Harned, Dr. David White, Daniel Caspi, and J. T. Mohr for helpful discussions, and Professor Mark T. Hamann for authentic samples and spectra of cyanthiwigins B, F, and G. Ruthenium olefin metathesis catalysts were generously donated by Materia.en
dc.publisherWiley-Blackwellen
dc.subjectasymmetric catalysisen
dc.subjectditerpeneen
dc.subjectnatural producten
dc.subjectpalladiumen
dc.subjecttotal synthesisen
dc.titleTotal Syntheses of Cyanthiwigins B, F, and Gen
dc.typeArticleen
dc.identifier.journalChemistry - A European Journalen
dc.identifier.pmcidPMC3365662en
dc.contributor.institutionThe Arnold and Mable Beckman Laboratories of Chemical Synthesis Department of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Blvd., MC 101-20, Pasadena, CA 91125, USA.en
kaust.grant.numberKUS-11-006-02en

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