文章基本信息

标题：Synthesis of Sceletium and Amaryllidaceae Alkaloids, (±) -Mesembrine and (±) -Dihydromaritidine, (±) -Epidihydromaritidine, (±) -Elwesine, and (±) -Epielwesine
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作者：OSAMU HOSHINO ; SHOHEI SAWAKI ; NAOMI SHIMAMURA 等
期刊名称：Chemical and Pharmaceutical Bulletin
印刷版ISSN：0009-2363
电子版ISSN：1347-5223
出版年度：1987
卷号：35
期号：7
页码：2734-2743
DOI：10.1248/cpb.35.2734
出版社：The Pharmaceutical Society of Japan
摘要：
The alkylation of 2-arylcyclohexanones (12b and 6) with alkyl halides or acrylonitrile and 50% aq. sodium hydroxide in the presence of a phase-transfer catalyst (18-crown-6) was found to give readily 2-alkyl-2-arylcyclohexanones (14 and 16) in fair to good yields. Furthermore, 2-allyl-2-aryl-5, 5-ethylenedioxycyclohexanone (16a or 16b) was coverted into (±) -mesembrine (1), (±) -dihydromaritidine (4a), and (±) -epidihydromaritidine (5a) or (±) -elwesine (dihydrocrinine) (4b) and (±) - epielwesine (5b), respectively, via 5, 5-ethylenedioxy-2-formylmethyl-2- (3', 4'-dimethoxy- or 3', 4'- methylenedioxyphenyl) cyclohexyl acetate (20a or 20b).
关键词：alkylation; 18-crown-6; 2-aryl-5, 5-ethylenedioxycyclohexanone; 2-allyl-2-aryl-5, 5-ethylenedioxycyclohexanone; (±) -mesembrine; (±) -dihydromaritidine; (±) -elwesine