Citation
Ag. Csaky et P. Vogel, 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 polyketides, TETRAHEDR-A, 11(24), 2000, pp. 4935-4944
Citations number
47
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166
→ ACNP
Volume
11
Issue
24
Year of publication
2000
Pages
4935 - 4944
Database
ISI
SICI code
0957-4166(200012)11:24<4935:SO1''R>2.0.ZU;2-P
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 resol
ved kinetically with Candida cylindracea lipase-catalysed transesterificati
on giving 1,1'-methylenedi[(1R, 1'R, 3R, 3'R, 5R, 5'R)-8-oxabicyclo[3.2.1]o
ct-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.