American Chemical Society
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Short Syntheses of Gabosine I and Gabosine G from δ-d-Gluconolactone

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journal contribution
posted on 2007-08-17, 00:00 authored by Tony K. M. Shing, Hau M. Cheng
A short synthesis of gabosine I (1) from δ-d-gluconolactone (3) in four steps, involving a one-pot TPAP oxidation−K2CO3-mediated intramolecular Horner−Wadsworth−Emmons (HWE) olefination as the key step, is described. Regioselective acetylation of the primary alcohol in gabosine I (1) then furnished gabosine G (2).