Studies on the asymmetric Birch reductive alkylation to access spiroimines

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• 作者：Thierry Jousseaume ; Pascal Retailleau ; Laurent Chabaud ; Catherine Guillou ; ^{guillou@icsn.cnrs-gif.fr}
• 关键词：Asymmetric Birch reductive alkylation ; Marine natural product ; Quaternary center ; Spiroimine
• 刊名：Tetrahedron Letters
• 出版年：2012
• 出版时间：14 March, 2012
• 年：2012
• 卷：53
• 期：11
• 页码：1370-1372
• 全文大小：571 K

文摘

The asymmetric Birch reductive alkylation has been investigated to synthesize spiroimine analogs of the neurophycotoxin (?-gymnodimine A 1. Two types of chiral aromatic substrates, an acyclic benzamide 2 and a benzoxazepinone 3 were studied. We found that the chiral auxiliary of benzoxazepinone could be easily removed in a three step procedure to afford ¦Â-ketoester 14 that was converted into spiroimines 23-24 possessing antagonist effects on nicotinic acetylcholine receptors (nAChRs).