BioChem - DOS

Stereoselective Enzymatic Reduction of Ethyl Secodione: Preparation of a Key Intermediate for the Total Synthesis of Steroids

European journal of organic chemistry

Contente, Martina Letizia; Molinari, Francesco; Serra, Immacolata; Pinto, Andrea; Romano, Diego

<P><B>Abstract</B></P><P>Ethyl secodione (<B>1</B>) has been enantioselectively reduced by using different biocatalysts for the preparation of ethyl secol (13<I>R</I>, 17<I>S</I>)&#8208;<B>2a</B>. The recombinant ketoreductase KRED1&#8208;Pglu converted the substrate with the highest reaction rate and stereoselectivity (<I>ee</I> > 98 %), whereas whole cells of <I>Pichia minuta</I> CBS 1708 showed the highest productivity. Stereoselective reduction of <B>1</B> provides the key chiral precursor for the synthesis of a number of hormonal contraceptives (i.e., desogestrel, norgestrel, gestodene).</P>

2016

WILEY&#x2010;VCH Verlag

1434-193x

1099-0690

2016

7

pp.1260-1263

10.1002/ejoc.201501557

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART75078205

Enzymatic reduction; Yeast; Steroids; Hormones; Enzymes