Premium
Stereoselective Enzymatic Reduction of Ethyl Secodione: Preparation of a Key Intermediate for the Total Synthesis of Steroids
Author(s) -
Contente Martina Letizia,
Molinari Francesco,
Serra Immacolata,
Pinto Andrea,
Romano Diego
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501557
Subject(s) - chemistry , stereoselectivity , gestodene , desogestrel , norgestrel , total synthesis , stereochemistry , enzyme , organic chemistry , catalysis , population , research methodology , demography , sociology , family planning
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 of 1 provides the key chiral precursor for the synthesis of a number of hormonal contraceptives (i.e., desogestrel, norgestrel, gestodene).