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 language | English |
---|---|
Pages (from-to) | 6562-6568 |
Journal | Organic and Biomolecular Chemistry |
Volume | 11 |
Issue number | 38 |
DOIs | |
Publication status | Published - 14 Oct 2013 |