Abstract
(−)-Elemoxide, a fragrant compound was synthesised using commercially available elemol in four steps with overall yield of 32%. The cyclic ether skeleton was constructed via intramolecular hydroalkoxylation using I2 and PhSiH3 catalytic system. Also, intramolecular oxymercuration-demercuration was employed as an alternate approach for cyclization. The various regioselective strategies involving epoxidation of alkene, reduction of epoxide and intramolecular cyclization were the highlights of the work. The key intermediate diol serves as a versatile intermediate for the synthesis of elemoxide and elemene.
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