Furanosteroid studies. Improved synthesis of the A, B, C, E-ring core of viridin

KC Mascall, PA Jacobi

Index: Mascall, Kristen C.; Jacobi, Peter A. Tetrahedron Letters, 2012 , vol. 53, # 13 p. 1620 - 1623

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Citation Number: 6

Abstract

The tetracyclic core skeleton of the furanosteroid viridin is prepared in nine steps from readily available materials. The key step in the synthesis is a facile acid-promoted cyclodehydration of an aryloxyketone to prepare the benzofuran moiety. From this intermediate, the known target skeleton is prepared in four steps. This new synthesis is a six- step improvement over the previously reported one.