A novel synthesis of (.+-.)-vermiculine

Y Fukuyama, CL Kirkemo, JD White

Index: Fukuyama,Y. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 646 - 647

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Citation Number: 30

Abstract

Dienol acetate 34 (1760, 1706 cm-I; 6 5.72 (1 H, s)), prepared from Hagemann's ester (2) by treatment with isopropenyl acetate containing p-toluenesulfonic acid (refl~ x),~ was reduced with sodium borohydride in aqueous dioxane (95 OC, 2 h) to hydroxy ester 4 (68%, 3500, 1710 cm-I; 6 3.98 (1 H, m)) and a minor quantity of the isomeric, allylic alcohol. 6 Further reduction of 4 with lithium aluminum hydride (ether, 0 OC, 6 h) afforded diol 5 (82%; 6 3.99 ...