D'Ambra T E, Javitt N B, Lacy J, Srinivasan P, Warchol T
Albany Molecular Research, Inc., 21 Corporate Circle, Albany, NY 12203, USA.
Steroids. 2000 Jul;65(7):401-7. doi: 10.1016/s0039-128x(00)00099-4.
We describe a convenient and stereoselective route to the synthesis of 27-hydroxycholesterol. Also its radiolabeled analog, 22, 23 di [(3)H]-27-hydroxycholesterol with high specific radioactivity (55 Ci/mmol) was synthesized by this method. Julia condensation of steroidal 22-sulfone with aldehyde, led to the addition of the 23-27 carbon side chain building block to the steroid backbone. Formed in this reaction beta-hydroxysulfone moiety was reduced by sodium amalgam generate 22-23 unsaturated bond. Further reduction either by hydrogen or tritium furnished substrates for the synthesis of title compounds.
