Tetrahedron

Syntheses of a prenylbisabolane diterpene, a natural insecticide from Croton linearis, and of the bisabolane sesquiterpenes (−)-delobanone and (−)-epi-delobanone

O Smitt, HE Högberg

Index: Smitt, Olof; Hoegberg, Hans-Erik Tetrahedron, 2002 , vol. 58, # 38 p. 7691 - 7700

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Citation Number: 22

Abstract

An enantioselective first total synthesis of a constituent of Croton linearis, the (−)-7-hydroxy- 3, 10-prenylbisaboladien-2-one 1, is described as well as the syntheses of the 7-hydroxy-3, 10-bisaboladien-2-ones (−)-epi-delobanone (14a) and (−)-delobanone (14b). The model compounds, 7-hydroxy-11-nor-methyl-3-bisabolen-2-one (8a), and 11, 15-nor-dimethyl-7- hydroxy-3-bisabolen-2-one (8b), were successfully prepared by opening of the protected ...