Development of an Enantiodivergent Strategy for the Total Synthesis of (+)- and (−)-Dragmacidin F from a Single Enantiomer of Quinic Acid

Garg, Neil K. and Caspi, Daniel D. and Stoltz, Brian M. (2005) Development of an Enantiodivergent Strategy for the Total Synthesis of (+)- and (−)-Dragmacidin F from a Single Enantiomer of Quinic Acid. Journal of the American Chemical Society, 127 (16). pp. 5970-5978. ISSN 0002-7863. doi:10.1021/ja050586v. https://resolver.caltech.edu/CaltechAUTHORS:20170222-093427303

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Abstract

An enantiodivergent strategy for the total chemical synthesis of both (+)- and (−)-dragmacidin F beginning from a single enantiomer of quinic acid has been developed and successfully implemented. Although unique, the synthetic routes to these antipodes share a number of key features, including novel reductive isomerization reactions, Pd(II)-mediated oxidative carbocyclization reactions, halogen-selective Suzuki couplings, and high-yielding late-stage Neber rearrangements.

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1021/ja050586v	DOI	Article
http://pubs.acs.org/doi/suppl/10.1021/ja050586v	Related Item	Supporting Information

ORCID:

Author	ORCID
Stoltz, Brian M.	0000-0001-9837-1528

Additional Information:

© 2005 American Chemical Society. Received 28 January 2005. Published online 2 April 2005. Published in print 1 April 2005. The authors thank the NIH-NIGMS (Grant R01 GM65961-01), the NDSEG (predoctoral fellowship to N.K.G.), Eli Lilly (predoctoral fellowship to D.D.C.), AstraZeneca, Boehringer Ingelheim, Johnson & Johnson, Pfizer, Merck, Amgen, Research Corp., Roche, and GlaxoSmithKline for generous funding. Drs. R. Riccio and A. Casapullo are acknowledged for an authentic sample of (−)-dragmacidin F. We also thank the Dervan and MacMillan laboratories for helpful discussions and the use of instrumentation.

Funders:

Funding Agency	Grant Number
NIH	R01GM65961-01
National Defense Science and Engineering Graduate (NDSEG) Fellowship	UNSPECIFIED
Eli Lilly	UNSPECIFIED
AstraZeneca	UNSPECIFIED
Boehringer-Ingelheim	UNSPECIFIED
Johnson and Johnson	UNSPECIFIED
Pfizer	UNSPECIFIED
Merck	UNSPECIFIED
Amgen	UNSPECIFIED
Research Corporation	UNSPECIFIED
Roche	UNSPECIFIED
GlaxoSmithKline	UNSPECIFIED

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DOI:

10.1021/ja050586v

Record Number:

CaltechAUTHORS:20170222-093427303

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20170222-093427303

Official Citation:

Development of an Enantiodivergent Strategy for the Total Synthesis of (+)- and (−)-Dragmacidin F from a Single Enantiomer of Quinic Acid Neil K. Garg, Daniel D. Caspi, and Brian M. Stoltz Journal of the American Chemical Society 2005 127 (16), 5970-5978 DOI: 10.1021/ja050586v

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ID Code:

74461

Collection:

CaltechAUTHORS

Deposited By:

Ruth Sustaita

Deposited On:

22 Feb 2017 19:29

Last Modified:

11 Nov 2021 05:27

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