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

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

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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).

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