STEREOSPECIFIC SYNTHESIS OF (+)-DECAHYDRO-ALPHA,ALPHA,4A-BETA-TRIMETHYL-BETA-CYCLOPROPA-[D]NAPHTHALENE-7-BETA-METHANOL

Recently, Mioss and co-workers2 reported the synthesis of the tricyclic alcohols 1 (β, β-cycloeudesmol) and 2 (α, β-cycloeudesmol). Independent syntheses of 1 and 2 as well as the tricyclic alcohol 3 (α, β-cycloeudesmol) have also been reported by Ando, Sayama, and Takase.3 Compounds 1-3 are diastereomers of the structure assigned to cycloeudesmol, an antibiotic cyclopropane containing sesquiterpene, which was isolated from the marine alga Chondria oppositiclada Dawson by Fenical and Sims.4 We wish to report an alternative stereospecific synthesis of the optically active alcohol 1 from the readily available terpene 2-carone (4)5. © 1979, American Chemical Society. All rights reserved.