Macrocycle formation by catalytic intramolecular cyclopropanation. a new general methodology for the synthesis of macrolides

MP Doyle, CS Peterson, MN Protopopova…

文献索引：Doyle, Michael P.; Peterson, Chad S.; Protopopova, Marina N.; Marnett, Alan B.; Parker Jr., Dann L.; Ene, Doina G.; Lynch, Vincent Journal of the American Chemical Society, 1997 , vol. 119, # 38 p. 8826 - 8837

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被引用次数: 54

摘要

Catalytic intramolecular cyclopropanation by diazoacetates onto a remote carbon-carbon double bond resulting in the formation of 9-to 20-membered ring lactones is reported. When competition exists between proximal allylic and remote olefinic cyclopropanation, macrocyclization is favored by catalysts of increasing electrophilicity: Rh2 (pfb) 4> Rh2 (OAc) 4, Cu (MeCN) 4PF6> Rh (cap) 4, and Cu (acac) 2. Terpene systems, cis-nerolidyl ...