Tetrahedron

Vitamin B 129 a catalyst in the synthesis of prostaglandins

S Busato, O Tinembart, R Scheffold

Index: Busato, Stephan; Tinembart, Olivier; Zhang, Zhong-da; Scheffold, Rolf Tetrahedron, 1990 , vol. 46, # 9 p. 3155 - 3166

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Abstract

A prostaglandin F2α precursor containing all structural features from C6 to C20 with 8R, 9S, 11R and 12R chirality is obtained by the one step formation of two CC bonds in the B12- catalyzed radical cyclization-addition sequence starting from a chiral cyclopentene bromoacetal and l-octyne-3-one. The B12-catalyzed radical cyclization-elimination sequence of a chiral cyclopentene precursor leads to (-)-(3aR, 6aS)-3, 3a, 6, 6a-tetrahydro ...