Asymmetric Total Synthesis of (+)-Luciduline: Toward a General Approach to Related Lycopodium Alkaloids

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• 作者：Guillaume Barbe ; Dominic Fiset ; Andre虂 B. Charette
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：July 1, 2011
• 年：2011
• 卷：76
• 期：13
• 页码：5354-5362
• 全文大小：985K
• 年卷期：v.76,no.13(July 1, 2011)
• ISSN：1520-6904

文摘

As part of a research program directed toward the synthesis of Lycopodium alkaloids, a multigram scale asymmetric synthesis of intermediate 11 was achieved in 11 steps from pyridine (17). In addition to our alkene metathesis strategy, a key feature of this synthetic approach consists of a Fukuyama鈥檚 Diels鈥揂lder cycloaddition between 1,2-dihydropyridine and acrolein using MacMillan鈥檚 catalyst (18) on a 50 g scale. This led to a 12-step catalytic asymmetric synthesis of (+)-luciduline (1). A broader subset of Lycopodium alkaloids could also be obtained, as demonstrated by the derivatization of 11 into advanced intermediates for the synthesis of some of these natural products.