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

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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.

Idioma original	Anglès
Pàgines (de-a)	4854-4857
Revista	Organic Letters
Volum	14
Número	18
DOIs	https://doi.org/10.1021/ol302185j
Estat de la publicació	Publicada - 21 de set. 2012

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@article{37240dd7b59a4962917a719f15b34a4a,

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.",

author = "Nuria Bardaj{\'i} and Francisco S{\'a}nchez-Izquierdo and Ram{\'o}n Alib{\'e}s and Josep Font and F{\'e}lix Busqu{\'e} and Marta Figueredo",

year = "2012",

month = sep,

day = "21",

doi = "10.1021/ol302185j",

language = "English",

volume = "14",

pages = "4854--4857",

number = "18",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/84868221207

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

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