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^*

^*この研究の対応する著者

研究成果: Article › 査読

10 被引用数 (Scopus)

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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.

本文言語	English
ページ（範囲）	801-804
ページ数	4
ジャーナル	Synlett
巻	1994
号	10
DOI	https://doi.org/10.1055/s-1994-23010
出版ステータス	Published - 1994 10月
外部発表	はい

ASJC Scopus subject areas

有機化学

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10.1055/s-1994-23010

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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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SN - 0936-5214

VL - 1994

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EP - 804

JO - Synlett

JF - Synlett

IS - 10

ER -

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

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