A total synthesis of racemic isoclovene (2), the most abundant sesquiterpene artifact derived from acid treatment of caryolan-1-ol (1), is presented. The characteristic tricyclo[6.2.2.05,12]dodecane skeleton of 2 has been set up creating the seven-membered ring C through an internal Michael addition of the suitably functionalized hydrindenone system 5. The latter was in turn obtained starting from the readily available cis-4,5,6,7,8,9-hexahydro-8-methylindan-1,5-dione (7) in 15 steps, the most significant of which was a [3,3]-sigmatropic rearrangement which allowed the establishment of the correct stereochemistry of the quaternary center at C-5. © 1985, American Chemical Society. All rights reserved.
Total Synthesis of (±)-Isoclovene
BARALDI, Pier Giovanni;BARCO, Achille;BENETTI, Simonetta;POLLINI, Gian Piero;POLO, Eleonora;SIMONI, Daniele
1985
Abstract
A total synthesis of racemic isoclovene (2), the most abundant sesquiterpene artifact derived from acid treatment of caryolan-1-ol (1), is presented. The characteristic tricyclo[6.2.2.05,12]dodecane skeleton of 2 has been set up creating the seven-membered ring C through an internal Michael addition of the suitably functionalized hydrindenone system 5. The latter was in turn obtained starting from the readily available cis-4,5,6,7,8,9-hexahydro-8-methylindan-1,5-dione (7) in 15 steps, the most significant of which was a [3,3]-sigmatropic rearrangement which allowed the establishment of the correct stereochemistry of the quaternary center at C-5. © 1985, American Chemical Society. All rights reserved.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
