Toward an Asymmetric Synthesis of the Dimeric Pyranonaphthoquinone Antibiotic Crisamicin A

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• 作者：Margaret A. Brimble ; Najmah P. S. Hassan ; Briar J. Naysmith ; Jonathan Sperry
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：August 1, 2014
• 年：2014
• 卷：79
• 期：15
• 页码：7169-7178
• 全文大小：649K
• ISSN：1520-6904

文摘

A full account of our efforts toward an asymmetric synthesis of crisamicin A are presented. The key steps include a Hauser鈥揔raus annulation of a cyanophthalide with a chiral enone-lactone, a stereoselective cyclization鈥搑eduction to install the pyran unit, and a Suzuki homocoupling to forge the key biaryl bond. This work has culminated in the asymmetric synthesis of a dimer bearing the complete carbon skeleton of the dimeric pyranonaphthoquinone natural product crisamicin A.