Tetrahedron Letters p. 2931 - 2934 (1999)
Update date:2022-09-26
Topics:
Robin, Jean-Pierre
Dhal, Robert
Dujardin, Gilles
Girodier, Laurent
Mevellec, Laurence
Poutot, Sandrine
(2'R,3S,4S,5R)-(-)-Homoharringtonine 2 was synthesized by direct esterification of cephalotaxine, using the activated forms of suitably substituted tetrahydropyrancarboxylic acids as sterically compact chiral side-chain precursors, followed by selective ring opening of the resulting (2'R,3S,4S,5R)-(-)-anhydrohomoharringtonine 6. Both enantiomers of the anhydro acyl moiety were prepared either by asymmetric α-hydroxyalkylation of the suitably substituted ethylenic α-ketoester 7 followed by acidic cyclisation, or by resolving the corresponding racemic mixture via formation of diastereomers with (-)quinine. Racemic cephalotaxine, as well as both its enantiomers, were prepared from natural - partially racemized - (-)- cephalotaxine 1.
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