Quinolizidines. XVI. Chiral syntheses of 9-demethylcephaeline and 10-demethylcephaeline

Quinolizidines. XVI. Chiral syntheses of 9-demethylcephaeline and 10-demethylcephaeline

フォーマット:

論文

責任表示:

Fujii, Tozo ; Ohba, Masashi

言語:

英語

出版情報:

日本薬学会, 1985-12-25

著者名:

掲載情報:

Chemical & pharmaceutical bulletin

ISSN:

0009-2363

巻:

33

通号:

12

開始ページ:

5264

終了ページ:

5269

バージョン:

publisher

概要:

In order to establish the structure of the Alangium alkaloid demethylcephaeline, chiral syntheses of the two possible alternative structures, (-)-9-demethylcephaeline (1) and (-)-10-demethylcephaeline (2), have been accomplished through a "cincholoipon-incorporating route." The synthesis of (-)-2 started with an initial condensation of the tricyclic acid (-)-12b, prepared from the ester (-)-11b by alkaline hydrolysis, with … 3-benzyloxy-4-methoxyphenethylamine and proceeded through the intermediates (-)-13b, (+)-15b, and (-)-14b. The 1'-epimers (-)-18b and (-)-17 were also produced in this reaction sequence. A parallel sequence of conversions starting with (+)-15a afforded (-)-1 via the intermediate (-)-14a, together with the 1'-epimer (-)-16 via (-)-18a. Unfortunately, however, lack of a sufficient amount of natural (-)-demethylcephaeline for a detailed and direct comparison precluded identification of either (-)-1 or (-)-2 with this alkaloid, leaving its chemistry incomplete. 続きを見る

URL:

http://hdl.handle.net/2297/7607

タイトル・著者・出版者が同じ資料

詳細

主題:	Bischler-Napieralski cyclization; NMR epimer differentiation; TLC epimer differentiation; benzyl ether catalytic hydrogenolysis; carbon-nitrogen double-bond catalytic reduction; demethylcephaeline; demethylisocephaeline; diethyl phosphorocyanidate amide formation
受理日:	1985-12-25

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