East Indian Sandalwood Oil. 2. Stereoselective Synthesis of (+/-)-Epi-β-santalene and (+/-)-Epi-β-santalol

Article abstract of DOI:10.1021/jo01303a026

Acid-catalyzed rearrangement of γ-lactone 6 in the presence of acetonitrile provides a mixture of amide acids, which are readily separated as their ethyl esters 18-20.The major product 18, when subjected to fragmentation, provides esters 21 and 22 (92percent and 8percent, respectively).The structure of 21 has been confirmed by its conversion, via aldehyde 23, to (+/-)-epi-β-santalene (8).Similarly, the structure of 22 has been confirmed by its conversion to (+/-)-α-santalene (3). (+/-)-Epi-cis-β-santalol (9), (+/-)-epi-trans-β-santalol (10), and (+/-)-dihydroepi-β-santalol (11) have also been prepared via aldehyd 23.