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

V.A. Khripach, V.N. Zhabinskii, A.I. Kuchto, Y.Y. Zhiburtovich, V.V. Gromak, M.B. Groen, J. van der Louw, Æ. de Groot

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20 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)6715-6718
JournalTetrahedron Letters
Issue number38
Publication statusPublished - 2006


  • medium-sized ring
  • secosteroids
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  • nmr
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