Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide

Gisela G. Bardají; Mariona Cantó; Ramón Alibés; Pau Bayón; Félix Busqué; Pedro De March; Marta Figueredo; Josep Font

doi:10.1021/jo801470u

Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide

Gisela G. Bardají, Mariona Cantó, Ramón Alibés, Pau Bayón, Félix Busqué, Pedro De March, Marta Figueredo, Josep Font

Department of Chemistry

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

38 Citations (Scopus)

Abstract

(Chemical Equation Presented) A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide. © 2008 American Chemical Society.

Original language	English
Pages (from-to)	7657-7662
Journal	Journal of Organic Chemistry
Volume	73
Issue number	19
DOIs	https://doi.org/10.1021/jo801470u
Publication status	Published - 3 Oct 2008

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title = "Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide",

abstract = "(Chemical Equation Presented) A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide. {\textcopyright} 2008 American Chemical Society.",

author = "Bardaj{\'i}, {Gisela G.} and Mariona Cant{\'o} and Ram{\'o}n Alib{\'e}s and Pau Bay{\'o}n and F{\'e}lix Busqu{\'e} and {De March}, Pedro and Marta Figueredo and Josep Font",

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doi = "10.1021/jo801470u",

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T1 - Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide

AU - Bardají, Gisela G.

AU - Cantó, Mariona

AU - Alibés, Ramón

AU - Bayón, Pau

AU - Busqué, Félix

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

PY - 2008/10/3

Y1 - 2008/10/3

N2 - (Chemical Equation Presented) A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide. © 2008 American Chemical Society.

AB - (Chemical Equation Presented) A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide. © 2008 American Chemical Society.

U2 - 10.1021/jo801470u

DO - 10.1021/jo801470u

M3 - Article

SN - 0022-3263

VL - 73

SP - 7657

EP - 7662

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide

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