Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
An Approach to Synthesis of Diterpenoid Alkaloids. III.
小木曾 彰清水 文治岩井 一成
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1963 年 11 巻 6 号 p. 770-774

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1-(p-Methoxyphenyl)-3, 5-dimethyl-3-azabicyclo [3. 3. 1] nonane-⊿9, α-acetaldehyde was synthesized from 1-(p-methoxyphenyl)-3, 5-dimethyl-3-azabicyclo [3. 3. 1] nonan-9-one (VI) by reaction with ethoxyethynyllithium and partial hydrogenation of the ethoxyethynyl carbinol (IX) followed by treatment with phosphorus tribromide. This α, β-unsaturated aldehyde would be a suitable starting material for the synthesis of diterpenoid alkaloids, because cyclization of a derivative having a tertiary hydroxyl group at C-9 position of the phenylazabicyclononane did not form an expected compound.
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© The Pharmaceutical Society of Japan
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