The Synthesis of Fenical and Sims' Structure of Cycloeudesmol. Stereospecific Total Syntheses of (+)-7β-(1-Hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene, (+)-7α-(1-Hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene, (+)-7β-(1-Hydr...

Article abstract of DOI:10.1021/jo00202a019

Stereospecific total syntheses of the four diastereoisomers of Fenical and Sims' structure of cycloeudesmol, (+)-7β-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene (Ia), (+)-7α-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene (Ib), (+)-7β-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aβ-decahydrocyclopropanaphthalene (Ic), and (+/-)-7α-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aβ-decahydrocyclopropanaphthalene (Id), were carried out with the object of establishing the structure of cycloeudesmol.The key step of these syntheses involves the Simmons-Smith reaction directed by the hydroxyl group at the allylic position or the homoallylic position.