A Modular Formal Total Synthesis of (±)-Cycloclavine

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• 作者：Natalie Netz ; Till Opatz
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：81
• 期：4
• 页码：1723-1730
• 全文大小：454K
• ISSN：1520-6904

文摘

Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence.