Synthetic Studies on Grayanotoxins Diastereofacially Selective Diels-Alder Reaction of 4-Benzyloxy-2-pentenoate

T. Kan, M. Oikawa, S. Hosokawa, M. Yanagiya, F. Matsuda, H. Shirahama

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The Diels-Alder reaction of methyl (2Z,4S)-4-(benzyloxy)-2-pentenoate (6) with 1-[(trimethylsilyl)oxy]-1,3-butadiene took place with complete 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 image of that of the C-ring of grayanotoxins, the main toxic substances in plant leaves belonging to the family Ericaceae.

Original languageEnglish
Pages (from-to)801-804
Number of pages4
JournalSynlett
Volume1994
Issue number10
DOIs
Publication statusPublished - 1994 Oct
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthetic Studies on Grayanotoxins Diastereofacially Selective Diels-Alder Reaction of 4-Benzyloxy-2-pentenoate'. Together they form a unique fingerprint.

  • Cite this