TOTAL SYNTHESIS OF (-)-VERRUCAROL, A COMPONENT OF NATURALLY-OCCURRINGVERRUCARIN-A

Authors
ISHIHARA J NONAKA R TERASAWA Y SHIRAKI R YABU K KATAOKA H OCHIAI Y TADANO K
Citation
J. Ishihara et al., TOTAL SYNTHESIS OF (-)-VERRUCAROL, A COMPONENT OF NATURALLY-OCCURRINGVERRUCARIN-A, Tetrahedron letters, 38(48), 1997, pp. 8311-8314
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
48
Year of publication
1997
Pages
8311 - 8314
Database
ISI
SICI code
0040-4039(1997)38:48<8311:TSO(AC>2.0.ZU;2-B
Abstract
Total synthesis of (-)-verrucarol (1) was achieved starting from D-glu cose-derived bicyclic lactone 4 through 1) a stereoselective asymmetri c quaternization of the a-carbon of the lactone, 2) Dieckmann cyclizat ion for access to the C-ring equivalent 3) a skeletal rearrangement fo r the trichothecene ring system, and 4) the final stereoselective epox idation of an exo-methylene group. (C) 1997 Elsevier Science Ltd.