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Intramolecular cycloaddition/cycloreversion of (E)-3β,17β-diacetoxy-5,10-secoandrost-1(10)-en-5-one |
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| Authors: | Vladimir A. Khripach Vladimir N. Zhabinskii Vladimir V. Gromak Jaap van der Louw |
| Affiliation: | a Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk, Belarus b Scientific Development Group, N.V. Organon, PO Box 20, 5340 BH Oss, The Netherlands c Wageningen University, Laboratory of Organic Chemistry, Dreijenplein 8, 6703 HB Wageningen, The Netherlands |
| Abstract: | Treatment of 3β,17β-diacetoxy-5,10-secoandrost-1(10)-en-5-one with BF3·Et2O was shown to proceed with cleavage of the macrocycle and formation of a new compound containing a cyclopentenone ring. Based on DFT calculations, an intramolecular Lewis acid promoted [2+2]cycloaddition, followed by a cycloreversion of the intermediate oxetane, is proposed as a possible reaction mechanism. |
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