Total synthesis of (+)-albicanol and (+)-albicanyl acetate.
The drimane sesquiterpenes, (+)-albicanol (2) and (+)-albicanyl acetate (3), were synthesized from an optically active bicyclic diol [(+)-1] that had been obtained via the recently developed optical resolution of a general synthetic intermediate for drimane sesquiterpenes. The crucial step in the previous syntheses was markedly improved by the modified Wittig methylenation of a silyloxy ketone (7). The high overall yield (77% in 4 or 5 steps from (+)-1) by this total synthesis makes it possible to synthesize the other biologically active drimane sesquiterpenes.
Toshima
H
H
Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan. toshima@chem.agr.hokudai.ac.jp
Oikawa
H
H
Toyomasu
T
T
Sassa
T
T
D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013057:Spectrum Analysis
D007659:Ketones; D009281:Naphthalenes; D012717:Sesquiterpenes; C438911:abicanyl acetate; C438910:albicanol