J. Rigby, N. C. Warshakoon, A. J. Payen
Aug 31, 1999
Citations
0
Influential Citations
40
Citations
Journal
Journal of the American Chemical Society
Abstract
A benzannulation sequence featuring [6π + 4π] cycloaddition of (η6-thiepin 1,1-dioxide)tricarbonylchromium(0) complexes with highly substituted dienes followed by Ramberg−Backlund rearrangement has been developed. Enantiomerically pure (+)-estradiol (estra-1,3,5(10)-triene-3,17β-diol) has been synthesized by employing a higher-order cycloaddition between an appropriately substituted thiepin dioxide chromium(0) complex and a diene partner derived from an enantiomerically pure indandione precursor as the key ring construction event. Subsequent Ramberg−Backlund rearrangement of this cycloadduct and routine functional group interchanges afforded the steroid target.