Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (−)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (−)-Cephalotaxine, and (+)-Cephalotaxine

Liu, Qi and Ferreira, Eric M. and Stoltz, Brian M. (2007) Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (−)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (−)-Cephalotaxine, and (+)-Cephalotaxine. Journal of Organic Chemistry, 72 (19). pp. 7352-7358. ISSN 0022-3263. doi:10.1021/jo0710883. https://resolver.caltech.edu/CaltechAUTHORS:20170215-155814896

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Abstract

A concise route toward the syntheses of (−)-drupacine and (+)- and (−)-cephalotaxine has been developed. The syntheses rely on Pd(II)-catalyzed aerobic oxidative heterocyclization chemistry, which was employed to rapidly construct an important spirocyclic amine intermediate. A dynamic β-elimination/conjugate addition process was strategically applied to complete the first asymmetric total synthesis of (−)-drupacine.

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1021/jo0710883	DOI	Article
http://pubs.acs.org/doi/suppl/10.1021/jo0710883	Publisher	Supporting Information

ORCID:

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

Additional Information:

© 2007 American Chemical Society. Received June 8, 2007; Publication Date (Web): August 18, 2007. We thank the NIH-NIGMS (R01 GM65961-01), Bristol-Myers Squibb Co. (graduate fellowship to E.M.F.), the NSF (graduate fellowship to E.M.F.), the Dreyfus Foundation, Merck Research Laboratories, Research Corporation, Abbott Laboratories, Pfizer, Amgen, GlaxoSmithKline, Lilly, and Johnson and Johnson for generous financial support. We are grateful to Ernie Cruz, Sandy Ma, and John Enquist for experimental assistance.

Funders:

Funding Agency	Grant Number
NIH	R01GM65961-01
Bristol-Myers Squibb Company	UNSPECIFIED
NSF Graduate Research Fellowship	UNSPECIFIED
Camille and Henry Dreyfus Foundation	UNSPECIFIED
Merck Research Laboratories	UNSPECIFIED
Research Corporation	UNSPECIFIED
Abbott Laboratories	UNSPECIFIED
Pfizer	UNSPECIFIED
Amgen	UNSPECIFIED
GlaxoSmithKline	UNSPECIFIED
Eli Lilly	UNSPECIFIED
Johnson and Johnson	UNSPECIFIED

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DOI:

10.1021/jo0710883

Record Number:

CaltechAUTHORS:20170215-155814896

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20170215-155814896

Official Citation:

Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (−)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (−)-Cephalotaxine, and (+)-Cephalotaxine Qi Liu, Eric M. Ferreira, and Brian M. Stoltz The Journal of Organic Chemistry 2007 72 (19), 7352-7358 DOI: 10.1021/jo0710883

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ID Code:

74349

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CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

16 Feb 2017 00:23

Last Modified:

11 Nov 2021 05:26

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