Author/Authors :
Khripach، نويسنده , , Vladimir A. and Zhabinskii، نويسنده , , Vladimir N. and Kuchto، نويسنده , , Anna I. and Zhiburtovich، نويسنده , , Yuliya Y. and Gromak، نويسنده , , Vladimir V. and Groen، نويسنده , , Marinus B. and van der Louw، نويسنده , , Jaap and de Groot، نويسنده , , Aede، نويسنده ,
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.
