[The synthesis of 2alpha,3alpha-isopropylidenedioxy-6,6-ethylenedioxy-5alpha-androst-15-en-17-one and its 2beta,3beta-isomer].
Androstane and delta15-androstane analogues of brassinosteroids were synthesized from dehydroepiandrosterone. The key stage, hydroxylation of 17beta-acetoxyandrost-2-en-6-one double bond with OsO4, yielded the corresponding 2alpha,3alpha- and 2beta,3beta-diols. The target 2alpha,3alpha-isopropylidenedioxy-6,6-ethylenedioxy-5alpha-androst-15-en-17-one and its 2beta,3beta-isomer were obtained by dehydrosilylation of the corresponding silylene ethers with palladium acetate.
R P
RP
Litvinovskaia
A V
AV
Baranovskiĭ
M A
MA
Aver'kova
V A
VA
Khripach
D000085:Acetates / Q000737:chemistry; D000736:Androstenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry; D009993:Osmium Tetroxide / Q000737:chemistry; D013237:Stereoisomerism
C523845:2,3-isopropylidenedioxy-6,6-ethylenedioxy-5alpha-androst-15-en-17-one; D000085:Acetates; D000736:Androstenes; D009942:Organometallic Compounds; C516071:palladium(II) acetate; D009993:Osmium Tetroxide