Diastereodivergent synthesis of the C8-C18 precursor and C1 '-C11 ' subunit of pamamycin 607 induced by a chiral sulfoxide group

Authors
Solladie, G Salom-Roig, XJ Hanquet, G
Citation
G. Solladie et al., Diastereodivergent synthesis of the C8-C18 precursor and C1 '-C11 ' subunit of pamamycin 607 induced by a chiral sulfoxide group, TETRAHEDR L, 41(15), 2000, pp. 2737-2740
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
15
Year of publication
2000
Pages
2737 - 2740
Database
ISI
SICI code
0040-4039(20000408)41:15<2737:DSOTCP>2.0.ZU;2-8
Abstract
A key step in obtaining the C8-C18 and C1'-C11' fragments of pamamycin 607, which differ by the syn- and anti-configuration of one chiral center alpha to the tetrahydrofuran ring, was the chelation controlled E-Z-isomerizatio n of the substituted vinyl tetrahydrofuran intermediate 3a which has so far been obtained only in the more stable E-configuration. (C) 2000 Elsevier S cience Ltd. Air rights reserved.