| Project/Area Number |
03555177
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| Research Category |
Grant-in-Aid for Developmental Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Nagoya Institute of Technology |
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Principal Investigator |
UENO Yoshio (1992) Nagoya Institute of Technology, Dept. of Applied Chem., Professor, 工学部, 教授 (70024297)
融 健 (1991) 名古屋工業大学, 工学部, 教授 (00163957)
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| Co-Investigator(Kenkyū-buntansha) |
TANAKA Toshio Teijin, Ltd, Ltd., Inst. for Biomedical research., Senio Researcher, 生物医学第1研究所, 主席研究員
ARAI Kazutaka Nissan chemical Industries, Ltd., Central Research Inst., Manager, 中央研究所, 部長
WATANABE Yoshihiko Nagoya Institute of Technology, Dept. of Applied Chem., Assistant Professor, 工学部, 助手 (70220944)
TORU Takeshi Nagoya Institute of Technology, Dept. of Applied Chen., Professor, 工学部, 教授 (00163957)
植野 禎夫 名古屋工業大学, 工学部, 教授 (70024297)
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| Project Period (FY) |
1991 – 1992
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| Project Status |
Completed (Fiscal Year 1992)
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| Budget Amount *help |
¥15,600,000 (Direct Cost: ¥15,600,000)
Fiscal Year 1992: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1991: ¥15,000,000 (Direct Cost: ¥15,000,000)
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| Keywords | Prostaglandin / Destannylselenenylation / Alkylcyloalkenone / Vinyl anion equivalent / Punaglandin / 2-アリル-2-シクロペンテノン / 脱シリルセレノ化反応 / 脱スタニルチオ化反応 / α-ケトビニルアニオン / 2-置換α、β-不飽和カルボニル |
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| Research Abstract |
This project deals with the study on the short and efficient synthesis of the synthetic intermediates of prostaglandins and punaglandins, both of which are known to have important biological activities related to the deseases of old people including cancer.
Treatment of 2-(phenylseleno)-2-cyclopenten(or cyclohexen)-1-one with tributylstannyllithium gave the enolate witch was then trapped with allyl iodide to afford the allylated cycloalkenone. Destannylselenenylation could be effected by numerous reagents such as tetrabutylammonium fluoride, bases, Lewis acids, or by thermal and photo treatments, giving 2-allyl-2-cylcoalken-1-one in high yields. According to this protocol, the key intermediate for prostaglandins and their analogs could be prepared in high yield directly from chiral 4-siloxy-2-cyclopenten-1-one. The method comprises the shortest and the most convenient process ever known. In the above procedure the phenylthio and trialkylsilyl groups were shown to be able to be substituted for the phenylseleno and the tributylstannyl groups, respectively.
The three-component coupling of 2-(phenylseleno)-2-cyclopenten-1-one, tributylstannyllithium, and aldehydes led to a high yield preparation of 2-(1-hydroxyalkyl)-2-cyclopenten-1-ones, which opened a way to the efficient synthesis of punaglandins and their analogs.
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