Flexible approach to stemona alkaloids: Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs

Nuria Bardají; Francisco Sánchez-Izquierdo; Ramón Alibés; Josep Font; Félix Busqué; Marta Figueredo

doi:10.1021/ol302185j

Flexible approach to stemona alkaloids: Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs

Nuria Bardají, Francisco Sánchez-Izquierdo, Ramón Alibés, Josep Font, Félix Busqué, Marta Figueredo

Department of Chemistry

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

15 Citations (Scopus)

Abstract

Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs have been completed through a flexible strategy devised for Stemona alkaloids. The azabicycle 7 is the pivotal intermediate, from which the sequence splits according to each particular target. The most remarkable differential feature for stemospironine is the installation of the spiranic γ-lactone through an intramolecular Horner-Wadsworth-Emmons olefination. The configuration of the stereogenic center at C-11 was controlled by fine-tuning of the synthetic sequence. © 2012 American Chemical Society.

Original language	English
Pages (from-to)	4854-4857
Journal	Organic Letters
Volume	14
Issue number	18
DOIs	https://doi.org/10.1021/ol302185j
Publication status	Published - 21 Sept 2012

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title = "Flexible approach to stemona alkaloids: Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs",

abstract = "Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs have been completed through a flexible strategy devised for Stemona alkaloids. The azabicycle 7 is the pivotal intermediate, from which the sequence splits according to each particular target. The most remarkable differential feature for stemospironine is the installation of the spiranic γ-lactone through an intramolecular Horner-Wadsworth-Emmons olefination. The configuration of the stereogenic center at C-11 was controlled by fine-tuning of the synthetic sequence. {\textcopyright} 2012 American Chemical Society.",

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T1 - Flexible approach to stemona alkaloids: Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs

AU - Bardají, Nuria

AU - Sánchez-Izquierdo, Francisco

AU - Alibés, Ramón

AU - Font, Josep

AU - Busqué, Félix

AU - Figueredo, Marta

PY - 2012/9/21

Y1 - 2012/9/21

N2 - Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs have been completed through a flexible strategy devised for Stemona alkaloids. The azabicycle 7 is the pivotal intermediate, from which the sequence splits according to each particular target. The most remarkable differential feature for stemospironine is the installation of the spiranic γ-lactone through an intramolecular Horner-Wadsworth-Emmons olefination. The configuration of the stereogenic center at C-11 was controlled by fine-tuning of the synthetic sequence. © 2012 American Chemical Society.

AB - Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs have been completed through a flexible strategy devised for Stemona alkaloids. The azabicycle 7 is the pivotal intermediate, from which the sequence splits according to each particular target. The most remarkable differential feature for stemospironine is the installation of the spiranic γ-lactone through an intramolecular Horner-Wadsworth-Emmons olefination. The configuration of the stereogenic center at C-11 was controlled by fine-tuning of the synthetic sequence. © 2012 American Chemical Society.

U2 - 10.1021/ol302185j

DO - 10.1021/ol302185j

M3 - Article

SN - 1523-7060

VL - 14

SP - 4854

EP - 4857

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Flexible approach to stemona alkaloids: Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs

Abstract

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