Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization.

Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization. Research Abstract Details 

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Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization. Abstract Text:

Takashi Ohshima,Youjun Xu,Ryo Takita,Satoshi Shimizu,Dafang Zhong,Masakatsu Shibasaki,

The enantioselective total synthesis of (-)-strychnine was accomplished through the use of the highly practical catalytic asymmetric Michael reaction (0.1 mol % of (R)-ALB, more than kilogram scale, without chromatography, 91% yield and >99% ee) as well as a tandem cyclization that simultaneously constructed B- and D-rings (>77% yield). Moreover, newly developed reaction conditions for thionium ion cyclization, NaBH3CN reduction of the imine moiety in the presence of Lewis acid to prevent ring opening reaction, and chemoselective reduction of the thioether (desulfurization) in the presence of exocyclic olefin were pivotal to complete the synthesis. The described chemistry paves the way for the synthesis of more advanced Strychnos alkaloids.

Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization. Publishing Authors By Initials

T Ohshima,Y Xu,R Takita,S Shimizu,D Zhong,M Shibasaki,

For similar heterocyclic compounds: alkaloids: indole alkaloids: secologanin tryptamine alkaloids: strychnine research abstracts see: heterocyclic compounds: alkaloids: indole alkaloids: secologanin tryptamine alkaloids: strychnine research

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Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Journal of the American Chemical Society

VOLUME: 124

Page Numbers: 14546-7

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 11

MONTH: Dec

YEAR: 2002

Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 7503056

Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization. Keywords Mesh Terms:

KEYWORDS: Strychnine

MESH TERMS: chemical synthesis

Chemical & Substance for Abstract: Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization. Information

Substance Name: Strychnine

Registry Number: 57-24-9

Grant and Affiliation Information for Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization.

AFFILIATION: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Country: United States

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MEDLINETA: J Am Chem Soc

REFSOURCE: J Am Chem Soc. 2003 Feb 19;125(7):2014

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