Stereoselective synthesis and relative configuration assignment of gabosine J

Miguel Ángel Fresneda, Ramon Alibés, Josep Font, Pau Bayón, Marta Figueredo

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15 Citations (Scopus)

Abstract

The first total synthesis of (+)-gabosine J and that of the epimer at C4 of its enantiomer have been accomplished through an enantioselective approach from a common intermediate 1. These syntheses have allowed us to establish the correct relative configuration of the natural metabolite, which was originally misassigned. This work, together with our former syntheses of other gabosines and related compounds, validates enone 1 as a general synthetic precursor for this kind of carbasugars. © 2012 American Chemical Society.
Original languageEnglish
Pages (from-to)5030-5035
JournalJournal of Organic Chemistry
Volume77
Issue number11
DOIs
Publication statusPublished - 1 Jun 2012

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