Synthesis of the pleuromutilin antibiotic SB-268091: A new practical and efficient synthesis of quinuclidine-4-thiol

B Choudary, RG Giles, F Jovic, N Lewis…

Index: Choudary, Bernie; Giles, Robert G.; Jovic, Florence; Lewis, Norman; Moore, Steve; Urquhart, Michael Organic Process Research and Development, 2012 , vol. 16, # 12 p. 1927 - 1939

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Citation Number: 4

Abstract

A synthesis of the pleuromutilin antibiotic SB-268091 is described which includes a new and improved route to the quinuclidine-4-thiol ligand. This chemistry has been run on multikilo scale and involved a reductive double debenzylation using sodium in liquid ammonia. Alternative conditions have been developed to prepare quinuclidine-4-thiol which avoid the use of sodium in liquid ammonia. The generality of this process to prepare differentially S- ...