Stereoselective Enzymatic Reduction of Ethyl Secodione: Preparation of a Key Intermediate for the Total Synthesis of Steroids. Issue 7 (18th February 2016)

• Record Type: Journal Article
• Authors: Contente, Martina Letizia; Molinari, Francesco; Serra, Immacolata; Pinto, Andrea; Romano, Diego
• Is Part Of: European journal of organic chemistry. Issue 7(2016)
• Page Start: 1260
• Page End: 1263
• Publication Date: 2016-02-18
• Subjects: Enzymatic reduction -- Yeast -- Steroids -- Hormones -- Enzymes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501557
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Ethyl secodione (1 ) has been enantioselectively reduced by using different biocatalysts for the preparation of ethyl secol (13 R, 17 S )‐2a . The recombinant ketoreductase KRED1‐Pglu converted the substrate with the highest reaction rate and stereoselectivity ( ee > 98 %), whereas whole cells of Pichia minuta CBS 1708 showed the highest productivity. Stereoselective reduction of1 provides the key chiral precursor for the synthesis of a number of hormonal contraceptives (i.e., desogestrel, norgestrel, gestodene). Abstract : Recombinant ketoreductase KRED1‐Pglu and whole cells of yeasts provide the key chiral precursor for the synthesis of a number of hormonal contraceptives (i.e., desogestrel, norgestrel, gestodene) with excellent stereoselectivity.