2 分子内Diels-Alder反応を用いるコルチコステロイド類の全合成(口頭発表の部)
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概要
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Total synthesis of (±)-11-oxoprogesterone(4), (±)-adrenosterone(5) and (±)-estrone(38) has been accomplished, and a synthesis of the (+)-trans-hydrindan(46) which is a potential intermediate for the synthesis of (+)-aldosterone(1) has been developed as an optically pure form using intramolecular Diels-Alder reaction as a key step. Total Synthesis of (±)-11-Oxoprogesterone(4) Thermolysis of the olefinic benzocyclobutene(10) afforded the trans-hydrindan(11) stereoselectively. The compound(11) was transformed into 11-oxoprogesterone(4), which is a known precursor of corticosteroids, via 19-nor-Δ^9-progesterone(18) and Δ^9-progesterone-(22). Total Synthesis of (±)-Adrenosterone(5) and (±)-Estrone(38) A conspicuously high diastereoselective synthesis of the trans-hydrindan(33) was achieved by the thermolysis of the ketal(28). The compound(33) was converted into the dienedione(37), which had been transformed into estrone(38) by S. Danishefsky. Also the trans-hydrindan(33) was transformed into (±)-adrenosterone(5) via the enedione(42) by a several-step sequence. Synthetic Approach to (+)-Aldosterone(1) A highly stereoselective synthesis of the (+)-trans-hydrindan(46) as an optically pure form has been accomplished by the thermolysis of the thioacetal(45c).
- 天然有機化合物討論会の論文
- 1987-07-25
著者
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福本 圭一郎
東北大・薬
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根本 英雄
東北大薬
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福本 圭一郎
東北大薬
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亀谷 哲治
星薬大
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亀谷 哲治
Institute Of Medicinal Chemistry Hoshi University
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永井 光雄
東北大薬
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