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Asymmetric synthesis of palitantin from the (5R)-tert-butyldimethylsiloxy-2-cyclohexenone

✍ Scribed by Georges Hareau; Masakazu Koiwa; Takeshi Hanazawa; Fumie Sato

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 238 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01549-x

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✦ Synopsis

+)-Palitantin (2) has been synthesized in 25% overall yield from the (5R)-tert-butyldimethylsiloxy-2cyclohexenone [(R)-I] where a remarkable diastereoselective cat. OsO4 cis-dihydroxylation of (R)-I 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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