Stereoselective, biogenetically patterned synthesis of (.+-.)-aplysistatin

JD White, T Nishiguchi, RW Skeean

Index: White; Nishiguchi; Skeean Journal of the American Chemical Society, 1982 , vol. 104, # 14 p. 3923 - 3928

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Citation Number: 30

Abstract

Abstract: A synthesis of (f)-aplysistatin (1) from geraniol is described, in which the key step is a biogenetically modeled cyclization of 24 to 26. Methyl (E)-homogeranylacetate (512) was converted to the tetronic acid 1Oc via chloroacetylation of the derived ketene acetal 7c, and 1Oc was sulfenylated and reduced to give 24. Cyclization of the latter with mercuric trifluoroacetate, followed by brominative substitution of mercury, yielded 26 with high ...