Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
An Approach to Synthesis of Diterpenoid Alkaloids. IV.
小木曾 彰清水 文治岩井 一成
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ジャーナル フリー

1963 年 11 巻 6 号 p. 774-779

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Catalytic reduction of 1-(p-methoxyphenyl)-3, 5-dimethyl-3-azabicyclo [3. 3. 1] nonane ⊿9, α-acetaldehyde (II) gave two epimeric saturated aldehydes (IIIa) and (IIIb). Both epimers were converted into the stereoisomeric hydrophenanthrene derivatives, VIa and VIb, respectively, by reduction with lithium aluminum hydride followed by cyclization with polyphospholic acid. The conformation of the stereoisomers was confirmed by determining the configuration of two epimeric alcohols (Va) and (Vb) from which these hydrophenanthrene compounds were derived. The A/B trans-fused isomer bears the common skeleton of the atisine-type alkaloids.
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© The Pharmaceutical Society of Japan
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