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Total Synthesis of (+)-Albicanol and (+)-Albicanyl Acetate via a Highly Diastereoselective Intramolecular Cycloaddition

DOI: 10.1039/P19900002481

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2481 - 2486 (1990)

Update date:2022-08-05

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Authors:

Shishido, KozoShishido, Kozo

Tokunaga, YujiTokunaga, Yuji

Omachi, NaomiOmachi, Naomi

Hiroya, KouHiroya, Kou

Fukumoto, KeiichiroFukumoto, Keiichiro

Kametani, TetsujiKametani, Tetsuji

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Article abstract of DOI:10.1039/P19900002481

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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Product name:(1S,2S)-methyl-(+)-2β-<2-(1,3-dioxolan-2-yl)ethyl>-1β,3,3-trimethylcyclohexanecarboxylate

Cas No:125265-48-7

125265-48-7

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