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The carboalkoxyallylsilane terminator for biomimetic polyene cyclizations. A route to 21-hydroxyprogesterone types
Affiliation:1. School of Chemistry, University of Wollongong, NSW 2522, Australia;2. Illawarra Health and Medical Research Institute, Wollongong, NSW 2522, Australia;1. Laboratory Physical Chemistry, Faculty of Sciences of Tetouan, University Abdelmalek Essaadi, Tetouan, Morocco;2. Laboratory of Physical Chemistry of Materials, Faculty of Sciences Ben M''Sik, Hassan II University of Casablanca, PO Box 7955 Sidi Othman, Casablanca, Morocco;1. End-Organ Disease Laboratories, Daiichi-Sankyo Co. Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan;2. Asubio Pharma Co. Ltd., 6-4-3 Minatojima-minamimachi Chuo-ku, Kobe-shi, Hyogo 650-0047, Japan;3. Modality Research Laboratories, Daiichi-Sankyo Co. Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan;4. Drug Metabolism & Pharmacokinetics Research Laboratories, Daiichi-Sankyo Co. Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan;5. Medicinal Safety Research Laboratories, Daiichi-Sankyo Co. Ltd., 1-16-13 Kitakasai Edogawa-ku, Tokyo 134-8630, Japan;1. Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, 103 Wenhua Road, Shenhe District, Shenyang 110016, PR China;2. Department of Pharmacology, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang 110016, PR China
Abstract:Polyene 3 containing a carboalkoxyallylsilane terminator was cyclized to give pro-steroid 6 in 68–75% yield. Unequivocal proof for the structure of 6 was obtained by conversion to the racemic form of the natural cortical hormone 17-desoxycorticosterone (15).
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