New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

Kazuo Tokuzaki; Yasuhiro Kanemitu; Takehiko Yoshimitsu; Hiroto Nagaoka

doi:10.1016/S0040-4039(00)00974-6

New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

Kazuo Tokuzaki, Yasuhiro Kanemitu, Takehiko Yoshimitsu, Hiroto Nagaoka

研究成果 › 査読

12 被引用数 (Scopus)

抄録

A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was constructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1- propionylcyclopentene (10) with ethyl cyclopropylidenacetate (3).

本文言語	English
ページ（範囲）	5923-5926
ページ数	4
ジャーナル	Tetrahedron Letters
巻	41
号	31
DOI	https://doi.org/10.1016/S0040-4039(00)00974-6
出版ステータス	Published - 7月 29 2000
外部発表	はい

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/S0040-4039(00)00974-6

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abstract = "A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was constructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1- propionylcyclopentene (10) with ethyl cyclopropylidenacetate (3).",

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T1 - New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

AU - Tokuzaki, Kazuo

AU - Kanemitu, Yasuhiro

AU - Yoshimitsu, Takehiko

AU - Nagaoka, Hiroto

PY - 2000/7/29

Y1 - 2000/7/29

N2 - A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was constructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1- propionylcyclopentene (10) with ethyl cyclopropylidenacetate (3).

AB - A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was constructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1- propionylcyclopentene (10) with ethyl cyclopropylidenacetate (3).

KW - Antitumor compounds

KW - Michael reactions

KW - Terpenes and terpenoids

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JO - Tetrahedron Letters

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New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

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