TOTAL SYNTHESIS OF (-)-TRANS-KUMAUSYNE

Authors
OSUMI K SUGIMURA H
Citation
K. Osumi et H. Sugimura, TOTAL SYNTHESIS OF (-)-TRANS-KUMAUSYNE, Tetrahedron letters, 36(32), 1995, pp. 5789-5792
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
32
Year of publication
1995
Pages
5789 - 5792
Database
ISI
SICI code
0040-4039(1995)36:32<5789:TSO(>2.0.ZU;2-N
Abstract
The total synthesis of (-)-trans-kumausyne has been accomplished in an enantiospecific fashion starting from an L-arabinose derivative. The key step is the stereoselective formation of the substituted tetrahydr ofuran via novel cyclization of the beta-silyl cation intermediate, ge nerated by the addition of allylsilane to di-O-isopropylidene-aldehydo -arabinose in the presence of boron trifluoride etherate.