SYNTHETIC STUDIES ON GRAYANOTOXINS - DIASTEREOFACIALLY SELECTIVE DIELS-ALDER REACTION OF 4-BENZYLOXY-2-PENTENOATE

Authors
KAN T OIKAWA M HOSOKAWA S YANAGIYA M MATSUDA F SHIRAHAMA H
Citation
T. Kan et al., SYNTHETIC STUDIES ON GRAYANOTOXINS - DIASTEREOFACIALLY SELECTIVE DIELS-ALDER REACTION OF 4-BENZYLOXY-2-PENTENOATE, Synlett, (10), 1994, pp. 801-804
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
10
Year of publication
1994
Pages
801 - 804
Database
ISI
SICI code
0936-5214(1994):10<801:SSOG-D>2.0.ZU;2-#
Abstract
The Diels-Alder reaction of methyl (2Z,4S)-4-(benzyloxy)-2-pentenoate (6) with 1-[(trimethylsilyl)oxy]-1,3-butadiene took place with complet e facial selectivity to give the epimeric mixture of the cycloadducts 8 and 9 (2:1). The absolute configuration of 8 and 9 is the mirror ima ge of that of the C-ring of grayanotoxins, the main toxic substances i n plant leaves belonging to the family Ericaceae.