A convenient chemoenzymatic synthesis of (1S,7aS)-1-hydroxy-5-oxo-4-(2 '-carboxyethyl)-7a-methyltetrahydro-indane - a key intermediate of steroids

摘要

A porcine pancreatic lipase mediated enzymatic hydrolysis of (+/-)-1-acetoxy-5-oxo-4-(2 '-carbomethoxyethyl)-7a-methyltetrahydroindane (5b) furnished (1S,7aS)-1-acetoxy-5-oxo-4-(2 '-carbomethoxyethyl)-7a-methyltetrahydro-indane (9) and (1R,7aR)-1-hydroxy-5-oxo-4-(2 '-carbomethoxyethyl)-7a-methyltetrahydro-indane (8) with > 99% e.e. which on further chemical hydrolysis gave 1 and ent-1, key intermediates of steroids. (c) 2006 Elsevier B.V. All rights reserved.