Santolinyl skeleton

Thomas, A. F., and W. Pawlak The Synthesis and Reactions of Yomogi Alcohol. Conversion of the Artemisyl Skeleton to the Santolinyl Skeleton by a 1,2-Shift of a Vinyl Group. Synthesis of Santolinatriene. Helv. Chim. Acta 54, 1822 (1971). 

A number of monoterpenes do not fit the isoprene mle and are called irregular monoterpenes. There are three major stmctural types of irregular monoterpenes the chrysan-themyl (89), artemisyl (90), and santolinyl (91) skeletons (Charlwood and Banthorpe, 1978 Charlwood and Chari-wood, 1991a). These compounds are found primarily in the Asteraceae (they are especially well known from the genus Artemisia), although a few are found in the Apiaceae and Lamiaceae (Poulter, 1990). As two skeletal types often occur in the same plant, it is reasonable to suspect that a common biosynthetic pathway exists and it is possible that the three types arise from a common cationic species (Fig. 19.21). 

Naturally occurring monoterpenes having a carbon skeleton other than head-to-tail, e. g. derivatives of the santolinyl, artemisyl and lavandulyl type, have formally been considered to be fission products of natural /m -chrysanthemic acid 28, 143). Compounds of the first two... 

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