A highly stereoselective synthesis of rel(1R, 3R, 7R, 9S)9-acetoxy-8,8-dimethyltricyclo(5.4.0.01,3)undecan-4-one, a versatile intermediate to terpenoids. Synthesis of .ALPHA.-onocerin.
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概要
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Hydrogenation of the tricyclic acetal 4, which was prepared from the octalone 3 by 2 steps, yielded the trans-dihydro product 5 with high stereoselectivity, while hydrogenation of the dimethyloctalones, 8 and 9, showed low stereoselectivity. 5 was converted to the cyclopropy-decalone 2 in high yield. Reductive alkylation of 2 gave regioselectively the C<SUB>1</SUB> alkylated trimethyldecalone 12, which was converted to the key intermediate to α-onocerin 16, thus illustrating potential utility of 2 in terpenoid synthesis.
- 社団法人 日本薬学会の論文
社団法人 日本薬学会 | 論文
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