Chemoenzymatic synthesis of (+)-totarol, (+)-podototarin, (+)-sempervirol, and (+)-jolkinolides E and D

Takahiro Miyake, Hideo Kigoshi, Hiroyuki Akita

doi:10.1016/j.tetasy.2007.11.024

Chemoenzymatic synthesis of (+)-totarol, (+)-podototarin, (+)-sempervirol, and (+)-jolkinolides E and D

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書誌事項

公開日: 2007-12

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DOI

10.1016/j.tetasy.2007.11.024

公開者: Elsevier BV

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説明

Abstract The enzymatic resolution products [(1 R ,4a R ,8a R )-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo- trans -naphthalene-1-methanol-2-ethylene acetal (8a R )- 7 (98% ee) and {acetate of (1 S ,4a S ,8a S )-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo- trans -naphthalene-1-methanol-2-ethylene acetal} (8a S )- 9 (>99% ee)] obtained by the lipase-catalyzed enantioselective acetylation of (±)- 7 in the presence of vinyl acetate as an acyl donor were converted to the α,β-unsaturated ketones (8a R )- 6 and (8a S )- 6 , respectively. Concise syntheses of (+)-totarol 1 , (+)-podototarin 2 and (+)-sempervirol 3 were achieved based on Michael reactions between (8a S )- 6 and the appropriate β-keto ester followed by aldol condensation. The first chiral syntheses of (+)-jolkinolides E 4 and D 5 were achieved from (5 R ,10 R ,12 R )-12-hydroxypodocarpa-8(14)-en-13-one 15 derived from (8a R )- 6 .