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Synthesis of the tetrahydrofuran unit of varitriol and γ- butyrolactones from 5-oxabicyclo[2.1.1]hexane derivative via oxidative cleavage reactions
S.H. Mahadevegowda,
Published in Elsevier Ltd
2014
Volume: 55
   
Issue: 14
Pages: 2266 - 2269
Abstract
A formal synthesis of marine-derived antitumor natural product varitriol from a 5-oxabicyclo[2.1.1]hexane derivative is described. A tetrahydrofuran unit of varitriol embedded with four contiguous stereocenters was synthesized with an overall yield of 10.2% in 11 steps from an oxa-bicyclic system. An unprecedented oxidative cleavage reaction involving scissoring of two CC bonds at oxa-quaternary carbon of THFs leading to γ-butyrolactones was reported and a plausible mechanism has been proposed. © 2014 Elsevier Ltd. All rights reserved.
About the journal
JournalData powered by TypesetTetrahedron Letters
PublisherData powered by TypesetElsevier Ltd
ISSN00404039