Stereoselctive Total Syntheses of Conduritols-F and -A from Tricyclo2,7>undeca-4,9-dien-3,6-dione

Article abstract of DOI:10.1016/0040-4039(95)00829-2

Effective syntheses of conduritols-F and A have been accomplished starting from cyclopentadiene/benzoquinone adduct 6.Key intermediates are tricyclic acetates 9 and 15 which, when subjected to flash vacuum thermolysis, afford epoxycyclohexene diacetate 10 and cyclohexadiene diacetate 17, respectively.Conduritol-F is obtained from 10 by hydrolysis while conduritol-A is produced from 17 by osmylation.In both cases the final step involves removal of the acetate groups by amidation with ammonia.