Literature DB >> 19007180

Highly diastereoselective Katsuki-Jacobsen oxidation-epoxidation of alpha-silyloxy sulfinyl dienes: synthetic applications.

Roberto Fernández de la Pradilla1, Alejandro Castellanos, Iñaki Osante, Ignacio Colomer, Mateo I Sánchez.   

Abstract

Katsuki-Jacobsen oxidation-epoxidation of acyclic alpha-silyloxy sulfinyl dienes, followed by acid-promoted cyclization, leads to 2,5-trans-sulfonyl dihydrofurans with good selectivities. As an application, the formal syntheses of (6S,7S,9R,10R)- and (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diols is reported.

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Year:  2009        PMID: 19007180     DOI: 10.1021/jo801803m

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


  1 in total

1.  An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.

Authors:  Sudeshna Roy; Christopher D Spilling
Journal:  Org Lett       Date:  2012-04-16       Impact factor: 6.005

  1 in total

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