Stereospecific Total Synthesis of (+/-)-Vetiselinenol

Article abstract of DOI:10.1021/jo00327a027

(+/-)-Vetiselinenol (1) and (+/-)-11-epivetiselinenol (12) have been synthesized by stereospecific routes using methyl lactones 4 and 3 to establish the desired stereochemistry at C-11.Equilibration studies indicated that the thermodynamic mixture of the lactones 3/4 is 45:55.Reductive opening of the lactones, selective acetylation, dehydration, and hydrolysis gave 1 and 12.Both 1 and 12 were converted to (+/-)-vetiselinene (15), establishing that they were indeed C-11 epimers.