A Chemoenzymatic Total Synthesis of (+)-Clividine

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• 作者：Lorenzo V. White ; Brett D. Schwartz ; Martin G. Banwell ; Anthony C. Willis
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：August 5, 2011
• 年：2011
• 卷：76
• 期：15
• 页码：6250-6257
• 全文大小：883K
• 年卷期：v.76,no.15(August 5, 2011)
• ISSN：1520-6904

文摘

The title compound, ent-1, the non-natural enantiomeric form of the lycorenine-type alkaloid (鈭?-clividine (1), has been prepared using the enantiomerically pure (ee >99.8%) cis-1,2-dihydrocatechol 3 as starting material. A key feature associated with the closing stages of the synthesis involved the diastereoselective addition of a nitrogen-centered radical onto a pendant cyclohexene to establish the cis-fused D-ring and the required stereochemistry at C11b in the final product ent-1.