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. doi:10.1021/ol401514s. 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:

URL	URL Type	Description
http://dx.doi.org/10.1021/ol401514s	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ol401514s	Publisher	Article
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3743267/	PubMed Central	Article

ORCID:

Author	ORCID
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 Agency	Grant Number
NIH	R01GM080269-01
Amgen	UNSPECIFIED
Abbott	UNSPECIFIED
Boehringer-Ingelheim	UNSPECIFIED
Caltech	UNSPECIFIED
NSF	CHE-0639094
NSF	CHE-1205646

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PubMed Central ID:

PMC3743267

DOI:

10.1021/ol401514s

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

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ID Code:

39890

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

13 Aug 2013 17:46

Last Modified:

09 Nov 2021 23:47

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