A stereoselective total synthesis of Δ9-progesterone via an intramolecular cycloaddition reaction |
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Authors: | Hideo Nemoto Mitsuo Nagai Keiichiro Fukumoto Tetsuji Kametani |
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Affiliation: | 1. Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan;2. Institute of Medicinal Chemistry, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142, Japan |
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Abstract: | A stereoselective total synthesis of 19-nor-Δ9(10)-progesterone (14) was achieved through des-A B-aromatic steroid (3) which was obtained by an intramolecular cycloaddition of the -quinodimethane generated from the thermolysis of 3-isopropenyl-5-(4-metho-xybenzocyclobutenyl)pentan-2-one-2-ethylene ketal (2), and the compound (14) thus obtained was further converted into Δ9-progesterone (18). |
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