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

doi:10.1055/s-1994-23010

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^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

10 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 language	English
Pages (from-to)	801-804
Number of pages	4
Journal	Synlett
Volume	1994
Issue number	10
DOIs	https://doi.org/10.1055/s-1994-23010
Publication status	Published - 1994 Oct
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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.",

author = "T. Kan and M. Oikawa and S. Hosokawa and M. Yanagiya and F. Matsuda and H. Shirahama",

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AU - Oikawa, M.

AU - Hosokawa, S.

AU - Yanagiya, M.

AU - Matsuda, F.

AU - Shirahama, H.

PY - 1994/10

Y1 - 1994/10

N2 - 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.

AB - 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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JO - Synlett

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IS - 10

ER -

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

Abstract

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