Synthesis of Optically Pure (R)-4a-Methyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone and Its Transformation into (+)-7-Hydroxycostal(Organic Chemistry)
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概要
- 論文の詳細を見る
A novel synthesis of the enone 12 starting from (+)-dihydrocarvone (3) and its transformation into (+)-7-hydroxycostal (1) are described. The ketone 10, obtained from 4 through a four-step sequence was converted to 12 by acid-catalyzed elimination and subsequent regioselective hydrogenation. Alternatively, the methoxyhydroperoxide 13 generated by the ozonolysis of 4 was subjected to the Criegee rearrangement, providing a mixture of 10 and 14, which on acid treatment, gave 11. Transformation of 12 into 19 was accomplished via a five-step reaction sequence. The reaction of 19 with the lithium alkoxide of 2-lithio-2-propenol afforded (+)-7-hydroxycostol (2), whose oxidation with manganese dioxide gave rise to (+)-7-hydroxycostal (1).
- 社団法人日本農芸化学会の論文
- 1988-08-23
著者
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Tanaka Akira
Department of Health and Nutrition, College of Human and Environmental Studies, Kanto-Gakuin Univers
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KAMATA Hirotoshi
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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Kamata H
Tohoku Univ. Miyagi Jpn
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Kamata Hirotoshi
Department Of Agricultural Chemistry Faculty Of Agriculture Tohoku University
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Tanaka Akira
Department Of Diagnostic Pathology Jichi Medical University
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TANAKA Akira
Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University
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