An effective enantioselective approach to the securinega alkaloids: Total synthesis of (-)-norsecurinine

Ramón Alibés; Pau Bayón; Pedro De March; Marta Figueredo; Josep Font; Elena García-García; David González-Gálvez

doi:10.1021/ol0522079

An effective enantioselective approach to the securinega alkaloids: Total synthesis of (-)-norsecurinine

Ramón Alibés, Pau Bayón, Pedro De March, Marta Figueredo, Josep Font, Elena García-García, David González-Gálvez

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

44 Citations (Scopus)

Abstract

(Chemical Equation Presented) A highly versatile approach to the enantioselective synthesis of securinega alkaloids is presented. Crucial steps are a palladium-catalyzed enantioselective imide alkylation, a vinylogous Mannich reaction, and a ring-closing metathesis process. Through this strategy, the synthesis of (-)-norsecurinine has been accomplished in nine steps and 11% overall yield. © 2005 American Chemical Society.

Original language	English
Pages (from-to)	5107-5109
Journal	Organic Letters
Volume	7
Issue number	22
DOIs	https://doi.org/10.1021/ol0522079
Publication status	Published - 27 Oct 2005

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10.1021/ol0522079

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title = "An effective enantioselective approach to the securinega alkaloids: Total synthesis of (-)-norsecurinine",

abstract = "(Chemical Equation Presented) A highly versatile approach to the enantioselective synthesis of securinega alkaloids is presented. Crucial steps are a palladium-catalyzed enantioselective imide alkylation, a vinylogous Mannich reaction, and a ring-closing metathesis process. Through this strategy, the synthesis of (-)-norsecurinine has been accomplished in nine steps and 11% overall yield. {\textcopyright} 2005 American Chemical Society.",

author = "Ram{\'o}n Alib{\'e}s and Pau Bay{\'o}n and {De March}, Pedro and Marta Figueredo and Josep Font and Elena Garc{\'i}a-Garc{\'i}a and David Gonz{\'a}lez-G{\'a}lvez",

year = "2005",

month = oct,

day = "27",

doi = "10.1021/ol0522079",

language = "English",

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An effective enantioselective approach to the securinega alkaloids: Total synthesis of (-)-norsecurinine. / Alibés, Ramón ; Bayón, Pau; De March, Pedro; Figueredo, Marta; Font, Josep; García-García, Elena; González-Gálvez, David.

In: Organic Letters, Vol. 7, No. 22, 27.10.2005, p. 5107-5109.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - An effective enantioselective approach to the securinega alkaloids: Total synthesis of (-)-norsecurinine

AU - Alibés, Ramón

AU - Bayón, Pau

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

AU - García-García, Elena

AU - González-Gálvez, David

PY - 2005/10/27

Y1 - 2005/10/27

N2 - (Chemical Equation Presented) A highly versatile approach to the enantioselective synthesis of securinega alkaloids is presented. Crucial steps are a palladium-catalyzed enantioselective imide alkylation, a vinylogous Mannich reaction, and a ring-closing metathesis process. Through this strategy, the synthesis of (-)-norsecurinine has been accomplished in nine steps and 11% overall yield. © 2005 American Chemical Society.

AB - (Chemical Equation Presented) A highly versatile approach to the enantioselective synthesis of securinega alkaloids is presented. Crucial steps are a palladium-catalyzed enantioselective imide alkylation, a vinylogous Mannich reaction, and a ring-closing metathesis process. Through this strategy, the synthesis of (-)-norsecurinine has been accomplished in nine steps and 11% overall yield. © 2005 American Chemical Society.

U2 - 10.1021/ol0522079

DO - 10.1021/ol0522079

M3 - Article

VL - 7

SP - 5107

EP - 5109

IS - 22

ER -