How a diversity-oriented approach has inspired a new hypothesis for the gabosine biosynthetic pathway. A new synthesis of (+)-gabosine C

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

Research output: Contribution to journalArticleResearchpeer-review

7 Citations (Scopus)

Abstract

A new synthesis of (+)-gabosine C has been accomplished as part of a general diversity-oriented approach that also delivered the previously unknown (-)-4-epi-gabosine C. The identification of the unexpected intermediate (+)-8, together with the isolation of ketones 9 and 10 in previous investigations, prompted us to formulate a new hypothesis for the biosynthesis of gabosines, based on a keto-enol equilibrium cascade pathway starting from 2-epi-5-epi-valiolone, along which the necessary precursors for all the different types of gabosines are generated. © 2013 The Royal Society of Chemistry.
Original languageEnglish
Pages (from-to)6562-6568
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number38
DOIs
Publication statusPublished - 14 Oct 2013

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