Intramolecular cycloaddition/cycloreversion of (E)-3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one

Intramolecular cycloaddition/cycloreversion of (E)-3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one

Treatment of 3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one with (BF3Et2O)-Et-. 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, follow...

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Veröffentlicht in:Tetrahedron letters 2006-09, Vol.47 (38)
Hauptverfasser: Khripach, V.A, Zhabinskii, V.N, Kuchto, A.I, Zhiburtovich, Y.Y, Gromak, V.V, Groen, M.B, Louw, J., van der, Groot, Æ., de
Format: Artikel
Sprache:eng
Schlagworte:
medium-sized ring
nmr
program
reactivity
secosteroids
steroids
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Zusammenfassung:Treatment of 3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one with (BF3Et2O)-Et-. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.07.096