Journal of the Chemical Society. Perkin transactions I p. 2481 - 2486 (1990)
Update date:2022-08-05
Topics:
Shishido, Kozo
Tokunaga, Yuji
Omachi, Naomi
Hiroya, Kou
Fukumoto, Keiichiro
Kametani, Tetsuji
The enantioselective total syntheses of the drimane-type sesquiterpenes albicanol (1) and albicanyl acetate (2) starting from (+)-Wieland-Miescher ketone (8) have been accomplished.The key step in the synthetic strategy involves a highly diastereoselective intramolecular <3+2> dipolar cycloaddition reaction of th nitrile oxide (6), which affords the isoxazoline (5) as the sole product in high yield.Reductive hydrolysis of compound (5) followed by methylenation of the resulting β-hydroxy ketone (4) by application of the Nozaki-Lombardo procedure provides (+)-albicanol (1), which is then converted into (+)-albicanyl acetate (2) by acetylation.The olefinic acetal (15), an intermediate of the present total synthesis, has been transformed by sequential Jones oxidation and methylation into a secosesquiterpene (17), one of the components of sun-cured Greek tabacco.
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