Synthesis of hexadeuterated 23-dehydroxybrassinosteroids.
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.
Khripach
Vladimir A
VA
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
Zhabinskii
Vladimir N
VN
Antonchick
Andrey P
AP
Konstantinova
Olga V
OV
Schneider
Bernd
B
D003903:Deuterium / Q000737:chemistry*; D015394:Molecular Structure; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*
D013260:Steroids, Heterocyclic; D003903:Deuterium