Quinolizidines. XV. A Racemic Synthesis of 10-Demethyltubulosine, an Alkaloid from Alangium lamarckii

Quinolizidines. XV. A Racemic Synthesis of 10-Demethyltubulosine, an Alkaloid from Alangium lamarckii

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, 1985-10-25

著者名:

掲載情報:

Chemical & pharmaceutical bulletin

ISSN:

0009-2363

巻:

33

通号:

10

開始ページ:

4314

終了ページ:

4319

バージョン:

publisher

概要:

The racemic synthesis of the Alangium lamarckii alkaloid 10-demethyltubulosine (2) has been accomplished for the first time via a "lactim ether route, "which included the intermediates (±)-7,(±)-8,(±)-10,and (±)-9. The 1'α-H isomers (±)-12 and (±)-11 were also obtained through this synthetic route. The assignments of the configuration at C-1'of … (±)-2,(±)-9,(±)-11,and (±)-12 were based on four criteria, namely, the ratio of products from the catalytic reduction of (±)-10,thin-layer chromatographic mobility, and ^1H and ^<13>C nuclear magnetic resonance spectral features. The identity of synthetic (±)-2 with (-)-demethyltubulosine from A. lamarckii unequivocally established the structure of this alkaloid. 続きを見る

URL:

http://hdl.handle.net/2297/7669

タイトル・著者・出版者が同じ資料

詳細

主題:	Alangium lamarckii alkaloid 10-demethyltubulosine; Bischler-Napieralski cyclization; NMR epimer differentiation; TLC epimer differentiation; benzyl ether catalytic hydrogenolysis; carbon-nitrogen double bond catalytic reduction; diethyl phosphorocyanidate amide formation
受理日:	1985-10-25

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