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Total Syntheses of Cyanthiwigins B, F, and G

Enquist, John A., Jr. and Virgil, Scot C. and Stoltz, Brian M. (2011) Total Syntheses of Cyanthiwigins B, F, and G. Chemistry: a European Journal, 17 (36). pp. 9957-9969. ISSN 0947-6539. PMCID PMC3365662. https://resolver.caltech.edu/CaltechAUTHORS:20111107-115520974

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/chem.201100425DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/chem.201100425/abstractPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3365662/PubMed CentralArticle
ORCID:
AuthorORCID
Virgil, Scot C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2011 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim. Received: February 8, 2011; Published online: July 18, 2011. 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.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)KUS-11-006- 02
NIHR01M080269-01
AmgenUNSPECIFIED
AbbottUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
MerckUNSPECIFIED
Bristol-Myers SquibbsUNSPECIFIED
GlaxoSmithKlineUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
PfizerUNSPECIFIED
NovartisUNSPECIFIED
RocheUNSPECIFIED
AstraZenecaUNSPECIFIED
CaltechUNSPECIFIED
Subject Keywords:asymmetric catalysis; diterpene; natural product; palladium; total synthesis
Issue or Number:36
PubMed Central ID:PMC3365662
Record Number:CaltechAUTHORS:20111107-115520974
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20111107-115520974
Official Citation:Enquist, J. A., Virgil, S. C. and Stoltz, B. M. (2011), Total Syntheses of Cyanthiwigins B, F, and G. Chemistry - A European Journal, 17: 9957–9969. doi: 10.1002/chem.201100425
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:27654
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:07 Nov 2011 21:23
Last Modified:09 Mar 2020 13:19

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