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.
|Publication status||Published - 2006|
- medium-sized ring