Bioactive Montanine Derivatives from Halide-induced Rearrangements of Haemanthamine-type Alkaloids. Absolute Configuration by VCD

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• 作者：Juan C. Cedrn^† ; ^‡ ; ; Ana Estvez-Braun*^† ; ^‡ ; ; ngel G. Ravelo*^† ; ^‡ ; ; David Gutirrez^§ ; ; Ninoska
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：April 2, 2009
• 年：2009
• 卷：11
• 期：7
• 页码：1491-1494
• 全文大小：141K
• 年卷期：v.11,no.7(April 2, 2009)
• ISSN：1523-7052

文摘

An unexpected rearrangement of haemanthamine-type alkaloids in the presence of halogenating agents has been found. Rearranged compounds present the 5,11-methanomorphantridine framework characteristic of montanine-type alkaloids. These compounds are difficult to obtain because of their scarcity in natural sources and because the synthetic approaches developed so far require numerous steps. Vibrational circular dichroism (VCD) spectroscopy was used to determine the absolute configuration of one of the rearranged compounds. Several rearranged alkaloids showed antimalarial activity.