Synthesis of the Core Tricyclic Ring Domain of (鈭?-Schulzeine B

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• 作者：Naoyuki Hoshiya ; Kenta Noda ; Yuji Mihara ; Nobuyuki Kawai ; Jun鈥檌chi Uenishi
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：August 7, 2015
• 年：2015
• 卷：80
• 期：15
• 页码：7790-7796
• 全文大小：418K
• ISSN：1520-6904

文摘

A formal synthesis of (鈭?-schulzeine B, a marine natural alkaloid possessing potent antidiabetic activity, has been achieved. A benzo[a]quinolizidin-4-one is a common skeleton of schulzeines (A鈥揅). (鈭?-Schulzeine B possesses an (S)-stereogenic center at the C-3 carbon. The chiral (3S,11bS)-3-amino-9,11-dimethoxybenzo[a]quinolizidin-4-one has been prepared efficiently from (2-bromo-3,5-dihydroxyphenyl)acetonitrile in 17 steps including (i) a dehydrative intramolecular amination catalyzed by HClO₄ and (ii) a proline or boric acid catalyzed transcycloamidation reaction for the construction of the 未-lactam ring.