Convenient Synthesis of 4-Acetyl-2-methoxy-5-methyltriacontane and 23-Hycilroxytriacontan-2-one, the Constituents of Curculigo orchioides

Bio-Organic Division, Bhabha, Atomic Research Centre, Trombay, Bombay-400 085

Unambiguous syntheses of the two title compounds (I) and (II), recently isolated by Mehta et al. and Misra et al. from Curculigo orehioides are reported. The syntheses use the Grignard coupling of undecenyl bromide with cetyl bromide (2) and monobromo­pyranyl ether (10) of dodecanediol, respectively as one of the key reactions. Further elaboration of the products in each case leads to the desired compounds (I) and (II). Complete identity of the synthetic products with the natural ones, however, could not be established.