title: Synthesis of hexadeuterated 23-dehydroxybrassinosteroids.
abstract: Two hexadeuterated brassinosteroids (BS) ([26,27-2H(6)]-23-dehydroxycastasterone and [26,27-2H(6)]-cathasterone) containing a hydroxy group at C(22) instead of the 22R,23R-diol function characteristic for most compounds of this class were prepared for biochemical studies. The corresponding non-deuterated compounds are considered intermediates in brassinolide biosynthesis. The carbon skeleton of the side chain with proper stereochemistry at C(24) was prepared from commercially available (2R)-3-hydroxy-2-methylpropanoate. This low molecular fragment was coupled to the tetracyclic steroidal fragment through the reaction of the appropriate sulfone with C(22) aldehyde. Formation of the necessary configuration of the 22-hydroxy group was achieved by hydride reduction of the corresponding ketone. Deuterium atoms at C(26) and C(27) originated from [2H(3)]methyl iodide used for alkylation of the intermediate sulfone.
authors.affiliation: Laboratory of Chemistry of Steroids, Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Street 5/2, 220141, Minsk, Belarus. hripach@iboch.bas-net.by
authors.forename: Vladimir A
authors.initials: VA
authors.lastname: Khripach
authors.forename: Vladimir N
authors.initials: VN
authors.lastname: Zhabinskii
authors.forename: Andrey P
authors.initials: AP
authors.lastname: Antonchick
authors.forename: Olga V
authors.initials: OV
authors.lastname: Konstantinova
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
mesh_terms: D003903:Deuterium / Q000737:chemistry*; D015394:Molecular Structure; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D013260:Steroids, Heterocyclic; D003903:Deuterium