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

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

Research output: Contribution to journalArticle

8 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 1
Externally publishedYes

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Poisons
Mirrors
1,3-butadiene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthetic Studies on Grayanotoxins Diastereofacially Selective Diels-Alder Reaction of 4-Benzyloxy-2-pentenoate. / Kan, T.; Oikawa, M.; Hosokawa, Seijiro; Yanagiya, M.; Matsuda, F.; Shirahama, H.

In: Synlett, Vol. 1994, No. 10, 01.10.1994, p. 801-804.

Research output: Contribution to journalArticle

Kan, T. ; Oikawa, M. ; Hosokawa, Seijiro ; Yanagiya, M. ; Matsuda, F. ; Shirahama, H. / Synthetic Studies on Grayanotoxins Diastereofacially Selective Diels-Alder Reaction of 4-Benzyloxy-2-pentenoate. In: Synlett. 1994 ; Vol. 1994, No. 10. pp. 801-804.
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