Synthesis of [26,27-2H6]brassinosteroids from 23,24-bisnorcholenic acid methyl ester.
A number of hexadeuterated brassinosteroids (BS) containing a hydroxy group at C-22 or a 22R,23R-diol function were prepared starting from 23,24-bisnorcholenic acid methyl ester for biosynthetic studies. Synthesis of the cyclic part was accomplished via the initial hydroboration-oxidation of Delta(5)-double bond. The key step in the synthesis of the side chain involved addition of (2S)-[3,4-(2)H(6)]2,3-dimethylbutylphenyl sulfone to the corresponding C-22 aldehydes.
Max-Planck-Institute for Chemical Ecology, Beutenberg Campus Winzerlaer Str. 10, D-07745 Jena, Germany.
Andrey P
AP
Antonchick
Bernd
B
Schneider
Vladimir N
VN
Zhabinskii
Vladimir A
VA
Khripach
D060406:Brassinosteroids; D002776:Cholestanes / Q000138:chemical synthesis* / Q000737:chemistry; D002777:Cholestanols / Q000138:chemical synthesis / Q000737:chemistry; D002778:Cholestanones / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D003903:Deuterium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009654:Norsteroids / Q000737:chemistry; D010840:Phytosterols / Q000138:chemical synthesis* / Q000737:chemistry; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000737:chemistry; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry
D060406:Brassinosteroids; D002776:Cholestanes; D002777:Cholestanols; D002778:Cholestanones; D009654:Norsteroids; D010840:Phytosterols; D010937:Plant Growth Regulators; D013260:Steroids, Heterocyclic; D003903:Deuterium; C023623:brassinolide