The chemistry of thujone. Part XIV. Synthesis of biologically active aryl terpenoid analogues

Carvalho, Chris ; Cullen, William R. ; Fryzuk, Michael D. ; Jacobs, Helen ; James, Brian R. ; Kutney, James P. ; Piotrowska, Krystyna ; Singh, Vinod K. (1989) The chemistry of thujone. Part XIV. Synthesis of biologically active aryl terpenoid analogues Helvetica Chimica Acta, 72 (2). pp. 205-212. ISSN 0018-019X

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/hlca.19...

Related URL: http://dx.doi.org/10.1002/hlca.19890720204

Abstract

Employing thujone-derived intermediates, a series of achiral (9a–d; Scheme 1) and chiral (11b and 11d;Scheme 2) terpene analogues related to the biologically active ‘terpenoid’ hybrids have been prepared. The stereochemistry of the key epoxidation reaction was established by correlation of the product 11b with the previously reported alcohol (R)-20 of known absolute configuration (Scheme 3).

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