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Synlett 1994; 1994(10): 801-804
DOI: 10.1055/s-1994-23010
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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
  • *Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060, Japan
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Publication Date:
22 March 2002 (online)

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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.

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