title: Synthesis of 3beta-hydroxy-androsta-5,7-dien-17-one from 3beta-hydroxyandrost-5-en-17-one via microbial 7alpha-hydroxylation.
abstract: The synthesis of 3beta-hydroxy-androsta-5,7-dien-17-one from 3beta-hydroxy-androst-5-en-17-one (dehydroepiandrosterone, DHEA) via microbial 7alpha-hydroxylation has been accomplished. At the first stage, 3beta,7alpha-dihydroxy-androst-5-en-17-one was obtained in high yield (71.2%) using a strain of Gibberella zeae VKM F-2600, which was first applied for DHEA conversion. The further route included the substitution of 7alpha-hydroxyl group with chlorine followed by a dehydrochlorination stage, and required minimal purifications of the intermediate products. The steroids obtained at every step were characterized by TLC,1H NMR, MS, UV- and IR-spectrometry. The combination of microbial and chemical steps ensured 54.6% yield of the target 3beta-hydroxy-androsta-5,7-dien-17-one from DHEA and can be applied for obtaining novel vitamin D derivatives.
authors.affiliation: G.K. Skryabin Institute of Biochemistry & Physiology of Microorganisms, Russian Academy of Sciences, Prospect Nauki 5, Pushchino, 142290 Moscow Region, Russia.
authors.forename: Tatyana G
authors.initials: TG
authors.lastname: Lobastova
authors.forename: Sergey M
authors.initials: SM
authors.lastname: Khomutov
authors.forename: Ljudmila L
authors.initials: LL
authors.lastname: Vasiljeva
authors.forename: Margarita A
authors.initials: MA
authors.lastname: Lapitskaya
authors.forename: Kasimir K
authors.initials: KK
authors.lastname: Pivnitsky
authors.forename: Marina V
authors.initials: MV
authors.lastname: Donova
mesh_terms: D000730:Androstadienes / Q000138:chemical synthesis*; D003687:Dehydroepiandrosterone / Q000737:chemistry* / Q000378:metabolism*; D005874:Gibberella / Q000378:metabolism*; D006900:Hydroxylation
chemical_list: D000730:Androstadienes; C039560:3-hydroxyandrosta-5,7-dien-17-one; D003687:Dehydroepiandrosterone