Synthesis of 1,1'-methylenedi[(1R,1'R,3R,3'R,5R,5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] and derivatives: precursors of long-chain polyketide
Csaky, A. G.; Vogel, P.
2000

Abstract

Racemic 1,1'-methylene[(1RS, 1'RS, 3RS, 3'RS, 5RS, 5'RS)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] ((+/-)-6) derived from 2,2'-methylenedifuran has been resolved kinetically with Candida cylindracea lipase-catalysed transesterification giving 1,1'-methylenedi[(1R, 1'R, 3R, 3'R, 5R, 5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] (-)-6 (30% yield, 98% ee) and 1,1'-methylenedi[(1S, 1'S, 3S, 3'S, 5S, 5'S)-8-oxabicyclo[3.2.1]oct-6-en-3-yl] diacetate (+)-8, (40% yield, 98% ee). These compounds have been converted into 1,1'-methylenedi[(4S, 4'S, 6S, 6'S)- and (4R, 4'R, 6R, 6'R)-cyclohept-1-en-4,6-diyl] derivatives. (C) 2001 Published by Elsevier Science Ltd.

Details

Title Synthesis of 1,1'-methylenedi[(1R,1'R,3R,3'R,5R,5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] and derivatives: precursors of long-chain polyketide
Author(s) Csaky, A. G. ; Vogel, P.
Published in Tetrahedron-Asymmetry
Volume 11
Issue 24
Pages 4935-4944
Date 2000
ISSN 0957-4166
Keywords
Note Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland.
DOI https://doi.org/10.1016/S0957-4166(00)00475-4
Laboratories LGSA
Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LGSA - Laboratory of Glycochemistry and Asymmetric Synthesis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2005-11-09

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