The Development of Strategies for Construction of the Aziridine Core of the Antitumor Agents Azinomycins A and B

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• 作者：Coleman ; Robert S. ; Carpenter ; Andrew J.
• 刊名：Tetrahedron
• 出版年：1997
• 出版时间：December 1, 1997
• 年：1997
• 卷：53
• 期：48
• 页码：16313-16326
• 全文大小：814 K

文摘

The synthesis of the C6-C13 aziridino[1,2a]pyrrolidine core substructure of the antitumor agents azinomycins A (1a) and B (1b) is described. Key synthetic steps included Wadsworth-Horner-Emmons olefination for formation of the C7-C8 double bond, an E-selective electrophilic bromination of the C8 position, and a stereospecific intramolecular addition-elimination reaction sequence for formation of the N-C8 pyrrolidine bond.