Enantioselective synthesis and absolute configuration assignment of gabosine O. synthesis of (+)- and (-)-gabosine N and (+)- and (-)-epigabosines N and O

Ramón Alibés, Pau Bayón, Pedro De March, Marta Figueredo, Josep Font, Georgina Marjanet

Research output: Contribution to journalArticleResearchpeer-review

38 Citations (Scopus)

Abstract

A rational approach to the synthesis of gabosines and other related carba-sugars starting from a masked p-benzoquinone has been designed. The enantioselective acetylation of the hydroxyketal 2 provides a practical entry to either enantiomer of the target products. The strategy has been applied to the synthesis of (+)- and (-)-gabosines N and O and (+)- and (-)-epigabosines N and O. The absolute configuration of natural gabosine O has been established. © 2006 American Chemical Society.
Original languageEnglish
Pages (from-to)1617-1620
JournalOrganic Letters
Volume8
Issue number8
DOIs
Publication statusPublished - 13 Apr 2006

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