Total synthesis of the putative structure of stemonidine: The definitive proof of misassignment

Francisco Sánchez-Izquierdo, Pilar Blanco, Félix Busqué, Ramón Alibés, Pedro De March, Marta Figueredo, Josep Font, Teodor Parella

Research output: Contribution to journalArticleResearchpeer-review

40 Citations (Scopus)

Abstract

The total synthesis of the putative structure of the Stemona alkaloid stemonidine has been completed. The key transformations include a 1,3-dipolar cycloaddition of a chiral nitrone derived from (S)-prolinol and a spirolactonization process involving the generation of the critical stereocenter. The NMR data of the synthetic material do not match those reported for the natural product. It is concluded that the structure assigned to stemonidine is incorrect, and it must be reassigned as stemospironine. © 2007 American Chemical Society.
Original languageEnglish
Pages (from-to)1769-1772
JournalOrganic Letters
Volume9
Issue number9
DOIs
Publication statusPublished - 26 Apr 2007

Fingerprint Dive into the research topics of 'Total synthesis of the putative structure of stemonidine: The definitive proof of misassignment'. Together they form a unique fingerprint.

Cite this