Structural Amendment and Stereoselective Synthesis of Mutisianthol.
cis-1-(5-Acetoxy-3,6-dimethyl-1-indanyl)-2-methyl-1-propene synthesized from 3,6-dimethyl-1-indanone was found to be different from mutisianthol by spectral comparison. The presence of a high-field signal in the NMR spectrum of the final product and various intermediates, characteristic of the cis-1,3-dialkylindanes but absent in the spectrum of the natural terpene, suggests a revision of the structure of mutisianthol to the trans isomer. The trans-indane which was subsequently obtained indeed exhibits data fully agreeable with mutisianthol. A similar stereochemical revision for jungianol is also indicated.
Ho
Tse-Lok
TL
Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan, Republic of China.
Lee
Kwang-Yuan
KY
Chen
Chun-Kuei
CK