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

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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
Issue number10
Publication statusPublished - 1994 Oct


ASJC Scopus subject areas

  • Organic Chemistry

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