Milbemycin-avermectin studies. 5. Total synthesis of milbemycin. beta. 3 and its C (12) epimer

SR Schow, JD Bloom, AS Thompson…

文献索引：Schow,S.R.; Bloom,J.D.; Thompson,A.S. Journal of the American Chemical Society, 1986 , vol. 108, p. 2662

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被引用次数: 81

摘要

Abstract: The total synthesis of milbemycin & (1) and its epimer, 12-epimilbemycin p3, is described. The central features of the synthetic strategy are (a) construction of the spiro ketal unit by nitrile oxide dipolar addition,(b) introduction of the requisite C (12) methyl center via a chelation-controlled cuprate addition in tandem with a stereocontrolled Ireland-Claisen rearrangement, and (c) construction of the southern hemisphere via a novel SN2'reaction ...