Enantioselective terpene synthesis based on R-(+)-limonene

Mehta, G. (1990) Enantioselective terpene synthesis based on R-(+)-limonene Pure and Applied Chemistry, 62 (7). pp. 1263-1268. ISSN 0033-4545

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Official URL: http://www.iupac.org/publications/pac/62/7/1263/

Related URL: http://dx.doi.org/10.1351/pac199062071263


The prevalence of a C12 - common core in diverse C15-C30 terpenes has been recognised. A bifun%onal C 12-cyclopentanoid derive 5 corresponding to this common-core has been prepared from R-(+)-limonene. The enantiomerically pure 5 has been elaborated to several sesqui- and diterpene skeleta. In particular, enantioselective syntheses of isodaucane sesquiterpene, (+)-aphanamol- I, 3 and a dolabellane diterpene, 6-araneosene 26 have been accomplished for the first time. A general solution to the stereochemical problem associated with this class of compounds has been devised. Syntheses of (-)- daucene 8 and (+)-isoamijiol 17 are also described.

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