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

Producción científica: Article › revisión exhaustiva

28 Citas (Scopus)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	8514-8517
Número de páginas	4
Publicación	Journal of Organic Chemistry
Volumen	69
N.º	24
DOI	https://doi.org/10.1021/jo048848j
Estado	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",

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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

UR - https://www.scopus.com/pages/publications/9344254954#tab=citedBy

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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