Quinolizidines. X. Stereospecific Syntheses of (±)-9-Demethylpsychotrine and (±)-10-Demethylpsychotrine

Quinolizidines. X. Stereospecific Syntheses of (±)-9-Demethylpsychotrine and (±)-10-Demethylpsychotrine

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, 1985-01-25

著者名:

掲載情報:

Chemical & pharmaceutical bulletin

ISSN:

0009-2363

巻:

33

通号:

1

開始ページ:

144

終了ページ:

151

バージョン:

publisher

概要:

With the aim of establishing the structure of the Alangium alkaloid desmethylpsychotrine, stereospecific syntheses of two alternative structures, (±)-9-demethylpsychotrine (1) and (±)-10-demethylpsychotrine (2), have been achieved through a"lactim ether route."The synthesis of (±)-1 started with an initial condensation of the lactim ether 6,derived from the translactam ester 5,with 3-benzyloxy-4-methoxyphenacyl bromide (7a) and … proceeded through the intermediates 8a, 9a, 10c, 10a, 11a, 12a, 13a, 14a, and 15a. A parallel sequence of conversions starting with 6 and 4-benzyloxy-3-methoxyphenacyl bromide (7b) produced (±)-2. The ^<13>C nuclear magnetic resonance spectra of (±)-1 and (±)-2 confirmed their endocyclic double bond structure in the dihydroisoquinoline moiety. Spectral comparison of (±)-1 and (±)-2 with natural desmethylpsychotrine suggested formula 1 to be the most likely structure of this alkaloid. 続きを見る

URL:

http://hdl.handle.net/2297/7611

タイトル・著者・出版者が同じ資料

詳細

主題:	Alangium alkaloid desmethylpsychotrine; Bischler-Napieralski cyclization; ^<13>C-NMR dihydroisoquinoline structure determination; benzyl ether cleavage; catalytic hydrogenolysis; diethyl phosphorocyanidate amide formation; lactim ether alkylation; sodium borohydride reduction; stereospecific synthesis
受理日:	1985-01-25

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