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Enantioselective Synthesis of the 5–6–7 Carbocyclic Core of the Gagunin Diterpenoids

Shibuya, Grant M. and Enquist, John A., Jr. and Stoltz, Brian M. (2013) Enantioselective Synthesis of the 5–6–7 Carbocyclic Core of the Gagunin Diterpenoids. Organic Letters, 15 (13). pp. 3480-3483. ISSN 1523-7060. PMCID PMC3743267. https://resolver.caltech.edu/CaltechAUTHORS:20130813-101335730

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Abstract

A catalytic enantioselective double allylic alkylation reaction has been employed in the synthesis of the core of the gagunin diterpenoids. Enantioenriched material was advanced in 11 steps to afford the core of the highly oxygenated target, which includes two all-carbon quaternary stereocenters.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol401514s DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol401514sPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3743267/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2013 American Chemical Society. Received May 29, 2013. Published on Web 06/26/2013. The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. Mr. Austin Moehle (Caltech) is thanked for the preparation of early compounds. Dr. David Vander Velde (Caltech) is gratefully acknowledged for assistance with the characterization of compounds by NMR spectroscopy. Mr. Lawrence Henling (Caltech) is gratefully acknowledged for X-ray crystallographic structural determination and Dr. Alexander Goldberg (Caltech) is acknowledged for assisting in the preparation of crystallographic images for publication. Ms. Kelly Kim (Caltech) is acknowledged for assistance with the IR data of a late-stage compound. Materia, Inc. and Dr. Keith Keitz (Caltech) are thanked for the generous donation of ruthenium catalysts. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094. We also wish to acknowledge helpful discussions with Christina White (UIUC), Huw Davies (Emory), and other members of the CCI Center for Selective C-H Functionalization supported by NSF (CHE-1205646).
Funders:
Funding AgencyGrant Number
NIHR01GM080269-01
AmgenUNSPECIFIED
AbbottUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
CaltechUNSPECIFIED
NSFCHE-0639094
NSFCHE-1205646
Issue or Number:13
PubMed Central ID:PMC3743267
Record Number:CaltechAUTHORS:20130813-101335730
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130813-101335730
Official Citation:Enantioselective Synthesis of the 5–6–7 Carbocyclic Core of the Gagunin Diterpenoids Grant M. Shibuya, John A. Enquist, Jr., and Brian M. Stoltz Organic Letters 2013 15 (13), 3480-3483
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:39890
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Aug 2013 17:46
Last Modified:03 Oct 2019 05:11

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