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13C NMR spectrum of 13 (δ 120 (CH), 168, 171) is consistent with the 2(5H)-furanone (butenolide) structure, not the 3(2H)-furanone: Guntrum, E.; Kuhn, W.; Spönlein, W.; Jäger, V. Synthesis 1986, 921. Sampson, P.; Roussis, V.; Drtina, G. J.; Koerwitz, F. L.; Wiemer, D. F. J. Org. Chem. 1986, 51, 2525. For the synthesis of steroidal spirobutenolides of opposite C-17 configuration, see: Kamata, S.; Haga, N.; Mitsugi, T.; Kondo, E.; Nagata, W.; Nakamura, M.; Miyata, K.; Odaguchi, K.; Shimizu, T.; Kawabata, T.; Suzuki, T.; Ishibashi, M.; Yamada, F. J. Med. Chem. 1985, 28, 428. For steroidal 3(2H)- furanones, see: Gupta, P. K.; Jones, J. G. Ll.; Caspi, E. J. Org. Chem. 1975, 40, 1420.
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13C NMR spectrum of 13 (δ 120 (CH), 168, 171) is consistent with the 2(5H)-furanone (butenolide) structure, not the 3(2H)-furanone: Guntrum, E.; Kuhn, W.; Spönlein, W.; Jäger, V. Synthesis 1986, 921. Sampson, P.; Roussis, V.; Drtina, G. J.; Koerwitz, F. L.; Wiemer, D. F. J. Org. Chem. 1986, 51, 2525. For the synthesis of steroidal spirobutenolides of opposite C-17 configuration, see: Kamata, S.; Haga, N.; Mitsugi, T.; Kondo, E.; Nagata, W.; Nakamura, M.; Miyata, K.; Odaguchi, K.; Shimizu, T.; Kawabata, T.; Suzuki, T.; Ishibashi, M.; Yamada, F. J. Med. Chem. 1985, 28, 428. For steroidal 3(2H)- furanones, see: Gupta, P. K.; Jones, J. G. Ll.; Caspi, E. J. Org. Chem. 1975, 40, 1420.
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13C NMR spectrum of 13 (δ 120 (CH), 168, 171) is consistent with the 2(5H)-furanone (butenolide) structure, not the 3(2H)-furanone: Guntrum, E.; Kuhn, W.; Spönlein, W.; Jäger, V. Synthesis 1986, 921. Sampson, P.; Roussis, V.; Drtina, G. J.; Koerwitz, F. L.; Wiemer, D. F. J. Org. Chem. 1986, 51, 2525. For the synthesis of steroidal spirobutenolides of opposite C-17 configuration, see: Kamata, S.; Haga, N.; Mitsugi, T.; Kondo, E.; Nagata, W.; Nakamura, M.; Miyata, K.; Odaguchi, K.; Shimizu, T.; Kawabata, T.; Suzuki, T.; Ishibashi, M.; Yamada, F. J. Med. Chem. 1985, 28, 428. For steroidal 3(2H)-furanones, see: Gupta, P. K.; Jones, J. G. Ll.; Caspi, E. J. Org. Chem. 1975, 40, 1420.
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0344891505
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note
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Two examples of A → B type alkylation in the presence of the A-ring dienone have been recorded: 24 → 25 in ref 2 (30% yield); Example 19 in U.S. Patent 3,862,194 (yield unspecified).
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