Literature DB >> 12762692

Stereoselective reactions of a (-)-quinic acid-derived enone: application to the synthesis of the core of scyphostatin.

Lynne M Murray1, Peter O'Brien, Richard J K Taylor.   

Abstract

[reaction: see text] A (-)-quinic acid-derived enone, with the trans-1,2-diol protected as a 2,3-dimethoxybutanediyldioxy ketal, provides an excellent template for further highly stereoselective elaboration as exemplified by its conversion into the core of scyphostatin, a potent inhibitor of neutral sphingomyelinase.

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Year:  2003        PMID： 12762692     DOI： 10.1021/ol034521d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  2 in total

1.  A strategy for the late-stage divergent syntheses of scyphostatin analogues.

Authors:  Jacob Y Cha; G Leslie Burnett; Yaodong Huang; Jarrod B Davidson; Thomas R R Pettus
Journal:  J Org Chem       Date:  2011-01-21       Impact factor: 4.354

2.  Synthesis of the B-seco limonoid core scaffold.

Authors:  Hanna Bruss; Hannah Schuster; Rémi Martinez; Markus Kaiser; Andrey P Antonchick; Herbert Waldmann
Journal:  Beilstein J Org Chem       Date:  2014-01-16       Impact factor: 2.883
  2 in total

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