The chemistry of Dodonaea SPP—IV

Tetrahedron
1973.0

Abstract

Further details are given for the assignment of absolute stereochemistry to the acetoxyhydroxy-acid (1) from D. attenuata and the lactone (6) from the var. linearis. The latter also provided a diene-acid shown to have structure 28. Reductive cyclisation of the tosylate of the latter gives a cyclopropane derivative (31). A flavone from the var. linearis is shown to be 5,7-dihydroxy-3,4',6-trimethoxyflavone (32). In 1967 we published a brief paper assigning structure and absolute stereochemistry to the acetoxy-hydroxy-acid (1) from Dodonaea attenuata A. Cunn. In addition, the var. linearis Benth. gave a lactone (6) which was inter-related with 1 and which we considered to be the lactone from hautriwaic acid which had been reported from D. viscosa in 1936. This view has since been confirmed by direct comparison of samples. In the last few years the structures of several other diterpenes have been assigned in this and other laboratories by inter-relation with 1 and 6 and we now wish to describe the isolation and structure assignment to some minor components. We also take this opportunity to present further details associated with the earlier article.

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