Tetrahedron letters

Regeneration of the milbemycin's C 2 C 4 structural arrangement from Δ 2-Milbemycin

S Naito, Y Owatari, A Saito

Index: Naito, Satoru; Owatari, Yuka; Saito, Akio Tetrahedron Letters, 1994 , vol. 35, # 42 p. 7797 - 7800

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Citation Number: 2

Abstract

Abstract An efficient methodology for converting Δ 2-milbemycin A 4 is described, whereby the Δ 2-isomer is initially converted to the C 2 epimer which in turn is epimerized at C 2 to its natural configuration. The key transformation is a Dess-Martin type oxidation at C 5 of the C 2 epimer in order to enhance the stability of the Δ 3-double bond and facilitate epimerization.