Abstract
The synthesis of abutasterone-type side chain, (20 R,22 R,24 S)-20,22,24,25-tetrahydroxy-6β-methoxy-3α,5- cyclo-5α-cholestane 4, and 24- epi-abutasterone-type side chain, (20 R,22 R,24 R)-20,22,24,25-tetrahydroxy-6β-methoxy-3α,5- cyclo-5α-cholestane 6, by means of Sharpless asymmetric dihydroxylation of ( E)-20(22),24-cholestadiene 1 is described. Construction of abutasterone-type side chain 4 was carried out by selective mono-dihydroxylation of diene 1 with (DHQ) 2AQN, followed by dihydroxylation of the corresponding (24 S)-hydroxy-20(22)-cholestene 2 with (DHQD) 2AQN. In contrast, bis-dihydroxylation of 1 with either (DHQD) 2PHAL or (DHQD) 2AQN preferentially occurs to produce 24- epi-abutasterone-type side chain 6.
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