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

Research output: Contribution to journalArticleResearchpeer-review

12 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 languageEnglish
Pages (from-to)4854-4857
JournalOrganic Letters
Volume14
Issue number18
DOIs
Publication statusPublished - 21 Sep 2012

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