Literature DB >> 17637067

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

Tony K M Shing1, Hau M Cheng.   

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).

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Year:  2007        PMID： 17637067     DOI： 10.1021/jo0709697

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  2 in total

1.  Allylic Strain as a Stereocontrol Element in the Hydrogenation of 3-Hydroxymethyl-cyclohex-3-en-1,2,5-triol Derivatives. Synthesis of the Carbasugar Pseudo-2-deoxy-α-D-glucopyranose.

Authors:  Peng Wen; David Crich
Journal:  Tetrahedron       Date:  2018-04-30       Impact factor: 2.457

2.  Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare.

Authors:  Yoshihide Usami; Hayato Ichikawa; Masao Arimoto
Journal:  Int J Mol Sci       Date:  2008-03-24       Impact factor: 6.208
  2 in total

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