251959-53-2Relevant articles and documents
Asymmetric synthesis of palitantin from the (5R)-tert-butyldimenthylsiloxy-2-cyclohexenone
Hareau, Georges,Koiwa, Masakazu,Hanazawa, Takeshi,Sato, Fumie
, p. 7493 - 7496 (2007/10/03)
(+)-Palitantin (2) has been synthesized in 25% overall yield from the (5R)-tert-butyldimethylsiloxy-2-cyclohexenone [(R)-1] where a remarkable diastereoselective cat. OsO4 cis-dihydroxylation of (R)-1 furnished the precursor of the optically pure (5R,6R)-bis-trimethylsiloxy 2-cyclohexenone (7) which underwent highly selectively the 1,4-addition reaction of the 1,3-heptadienyl cyanocuprate to give, after trapping of the corresponding copper enolate with formaldehyde, the target compound.