Terpenes and Terpene Derivatives, XXIX. Synthesis and Olfactive Properties of (—)??and rac??Silphiperfol??5??en??3??ol and of Some Tris??nor Derivatives

P Weyerstahl, J Brendel

Index: Weyerstahl, Peter; Brendel, Joachim Liebigs Annalen der Chemie, 1992 , # 7 p. 669 - 678

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Citation Number: 6

Abstract

Abstract The new sesquiterpene alcohols silphiperfol-5-en-3-ol [(—)-1a] and the corresponding 7-epi compound (+)-1b, important constituents of the essential oil of Artemisia laciniata have been synthesized in 13 steps by starting from (R)-(+)-pulegone (6) in an overall yield of 8%. The key reaction is the coppercatalyzed 1, 4-Grignard addition of the iodo acetal 34 to the enone (+)-4 in the presence of TMSCI and TMEDA to give the silyl ...