Total Syntheses of (±)-Cephalotaxine and (±)-8-Oxocephalotaxine

Martin E. Kuehne, William G. Bornmann, William H. Parsons, Timothy D. Spitzer, J. F. Blount, J. Zubieta

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Abstract

A synthesis of (±)-cephalotaxine (1) was obtained based on a novel oxidative rearrangement of the bicyclic enamide 5 to the spirocyclopentanone lactam 20. The overall yield from keto ester 6 and amine 7 was 28%, in nine steps, or 41% in ten steps. Double-bond isomerization of minor side product ene lactam 9, with formation of the key ene lactam intermediate 5, increased the overall yields of the synthesis to 45% (nine steps) or 66% (ten steps). The racemate of the natural product 8-oxocephalotaxine (40) was obtained in an alternative last step by a selective reduction of the keto lactam 39.

Original languageEnglish (US)
Pages (from-to)3439-3450
Number of pages12
JournalJournal of Organic Chemistry
Volume53
Issue number15
DOIs
StatePublished - Feb 1 1988
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Kuehne, M. E., Bornmann, W. G., Parsons, W. H., Spitzer, T. D., Blount, J. F., & Zubieta, J. (1988). Total Syntheses of (±)-Cephalotaxine and (±)-8-Oxocephalotaxine. Journal of Organic Chemistry, 53(15), 3439-3450. https://doi.org/10.1021/jo00250a008