55023-27-3Relevant academic research and scientific papers
Synthesis of the pleuromutilin antibiotic SB-268091: A new practical and efficient synthesis of quinuclidine-4-thiol
Choudary, Bernie,Giles, Robert G.,Jovic, Florence,Lewis, Norman,Moore, Steve,Urquhart, Michael
, p. 1927 - 1939 (2013/03/13)
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-protected quinuclidine-4-thiols is also discussed and exemplified by the preparation of a range of analogues.
