SYNTHETIC STUDIES ON THE TRICHOTHECENE FAMILY FROM D-GLUCOSE

Authors
ISHIHARA J NONAKA R TERASAWA Y TADANO K OGAWA S
Citation
J. Ishihara et al., SYNTHETIC STUDIES ON THE TRICHOTHECENE FAMILY FROM D-GLUCOSE, Tetrahedron : asymmetry, 5(11), 1994, pp. 2217-2232
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
11
Year of publication
1994
Pages
2217 - 2232
Database
ISI
SICI code
0957-4166(1994)5:11<2217:SSOTTF>2.0.ZU;2-6
Abstract
Base-catalyzed intramolecular cyclization of D-glucose-derived substra te 10 provided a diastereomeric mixture of bicyclic beta-hydroxyl dies ters 6R and 6S. Further functionalization of the mixture afforded an e nantiomerically pure bicyclic lactone 4. A double alkylation of 4 prov ided 3 stereoselectively. Dieckmann cyclization of a lactone-ester 2, which was prepared from 3, followed by protection of a hemiacetal hydr oxyl group provided smoothly a tricyclic compound 1.