Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: Application to the synthesis of (-)-sedamine

Guangrong Zheng; Linda P. Dwoskin; Peter A. Crooks

doi:10.1021/jo048848j

Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: Application to the synthesis of (-)-sedamine

Guangrong Zheng, Linda P. Dwoskin, Peter A. Crooks

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28 Scopus citations

Abstract

Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (-)-lobeline to (-)-sedamine in high overall yield.

Original language	English
Pages (from-to)	8514-8517
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	69
Issue number	24
DOIs	https://doi.org/10.1021/jo048848j
State	Published - Nov 26 2004

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Author National Institute on Drug Abuse DA031791 Mark J Ferris National Institute on Drug Abuse DA006634 Mark J Ferris National Institute on Alcohol Abuse and Alcoholism AA026117 Mark J Ferris National Institute on Alcohol Abuse and Alcoholism AA028162 Elizabeth G Pitts National Institute of General Medical Sciences GM102773 Elizabeth G Pitts Peter McManus Charitable Trust Mark J Ferris National Institute on Drug Abuse

R01DA013519

Author National Institute on Drug Abuse DA031791 Mark J Ferris National Institute on Drug Abuse DA006634 Mark J Ferris National Institute on Alcohol Abuse and Alcoholism AA026117 Mark J Ferris National Institute on Alcohol Abuse and Alcoholism AA028162 Elizabeth G Pitts National Institute of General Medical Sciences GM102773 Elizabeth G Pitts Peter McManus Charitable Trust Mark J Ferris National Institute on Drug Abuse

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Organic Chemistry

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title = "Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: Application to the synthesis of (-)-sedamine",

abstract = "Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (-)-lobeline to (-)-sedamine in high overall yield.",

author = "Guangrong Zheng and Dwoskin, \{Linda P.\} and Crooks, \{Peter A.\}",

year = "2004",

month = nov,

day = "26",

doi = "10.1021/jo048848j",

language = "English",

volume = "69",

pages = "8514--8517",

number = "24",

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TY - JOUR

T1 - Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline

T2 - Application to the synthesis of (-)-sedamine

AU - Zheng, Guangrong

AU - Dwoskin, Linda P.

AU - Crooks, Peter A.

PY - 2004/11/26

Y1 - 2004/11/26

N2 - Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (-)-lobeline to (-)-sedamine in high overall yield.

AB - Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (-)-lobeline to (-)-sedamine in high overall yield.

UR - https://www.scopus.com/pages/publications/9344254954

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U2 - 10.1021/jo048848j

DO - 10.1021/jo048848j

M3 - Article

C2 - 15549833

AN - SCOPUS:9344254954

SN - 0022-3263

VL - 69

SP - 8514

EP - 8517

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: Application to the synthesis of (-)-sedamine

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