Short syntheses of gabosine I and gabosine G from delta-D-gluconolactone

Tony K M Shing; Hau M Cheng

doi:10.1021/jo0709697

Short syntheses of gabosine I and gabosine G from delta-D-gluconolactone

J Org Chem. 2007 Aug 17;72(17):6610-3. doi: 10.1021/jo0709697. Epub 2007 Jul 19.

Authors

Tony K M Shing¹, Hau M Cheng

Affiliation

¹ Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, Hong Kong, China. tonyshing@cuhk.edu.hk

PMID: 17637067
DOI: 10.1021/jo0709697

Abstract

A short synthesis of gabosine I (1) from delta-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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclohexanones / chemical synthesis*
Gluconates / chemistry*
Lactones
Magnetic Resonance Spectroscopy
Spectrometry, Mass, Electrospray Ionization
Spectrometry, Mass, Fast Atom Bombardment

Substances

Cyclohexanones
Gluconates
Lactones
gabosine G
gabosine I
beta-glucono-1,5-lactone