Direct formation of the steroid nucleus by a biomimetic cyclization

WS Johnson, BE McCarry, RL Markezich…

Index: Johnson, William S.; McCarry, Brian E.; Markezich, R. L.; Boots, Sharon G. Journal of the American Chemical Society, 1980 , vol. 102, # 1 p. 352 - 359

Full Text: HTML

Citation Number: 27

Abstract

Abstract: The aim of this study was to synthesize the trienynol 3 and to study its cyclization. The substrate was synthesized by a convergent route, the key step being the stereoselective Wittig-Schlosser condensation of the known4 aldehyde 19 with the phosphorane 18 (synthesized as shown in Scheme I). The product 20 was converted in two steps to the trienynol 3 as depicted in Scheme 111. Resolution of the acid 10 by crystallization of the ...