Alternative Synthesis of (±)-Trisporol B via (±)-6-Hydroxymethyl-2,6-dimethyl-2-cyclohexen-1-one(Organic Chemistry)
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概要
- 論文の詳細を見る
(±)-Methyl 1,3-dimethyl-2-oxo-3-cyclohexene-1-carboxylate (7) was synthesized from methyl propionate via Claisen condensation followed by Robinson annelation with acrolein. Lithium aluminum hydride reduction and manganese dioxide oxidation of 7 gave (±)-6-hydroxymethyl-2,6-dimethyl-2-cyclohexen-1-one (3), which is a useful new building block for natural product syntheses. Next, 3 was converted to (±)-8'-acetoxy-3'-oxo-β-ionone (16). A wittig reaction of 16 with 3-(2-methyl-1,3-dioxolan-2-yl)propylidenetriphenylphosphorane in tetrahydrofuran, with subsequent deprotection, afforded the fungal sexual prohormone(±)-(7E, 9Z)-trisporol B (1), and its (9E)-isomer (19).
- 社団法人日本農芸化学会の論文
- 1987-04-23
著者
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YAMASHITA Kyohei
Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University
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ORITANI Takayuki
Department of Applied Biological Chemistry, Faculty of Agriculture
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Takahashi Shozo
Pesticide Research Institute Kyoto University
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Takahashi Shunya
Riken(the Institute Of Physical And Chemical Research)
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Yamashita K
Tohoku Univ. Sendai Jpn
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Takahashi S
Nihon Univ. Chiba Jpn
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TAKAHASHI Shunya
Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University
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Yamashita Kyohei
Department Of Agricultural Chemistry Faculty Of Agriculture Tohoku University
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Oritani Takayuki
Department Of Agricultural Chemistry Faculty Of Agriculture Tohoku University
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Takahashi S
Riken(the Institute Of Physical And Chemical Research)
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