Asymmetric synthesis of palitantin (cas 15265-28-8) from the (5R)-tert-butyldimethylsiloxy-2-cyclohexenone

Add time:08/04/2019    Source:sciencedirect.com

(+)-palitantin (cas 15265-28-8) (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.

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