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Synlett 1999; 1999(10): 1555-1558
DOI: 10.1055/s-1999-2889
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Diastereoselective Synthesis of a seco-Taxane

Damien Bourgeois* , Jean-Yves Lallemand, Ange Pancrazi, Joëlle Prunet
  • *Laboratoire de Synthèse Organique, associé au CNRS, Ecole Polytechnique, DCSO, 91128 Palaiseau, France; Fax (33)1 69 33 30 10; E-mail: Joelle.Prunet@polytechnique.fr
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Publikationsdatum:
31. Dezember 1999 (online)

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Ketone 9 was synthesized in 7 steps from commercially available 2-methylcyclohexane-1,3-dione in a diastereoselective fashion. Shapiro reaction of easily available trisylhydrazone 11 with benzaldehyde was used as a model for A- and C-ring coupling. Finally, reaction of trisylhydrazone 24 with A-ring aldehyde 4, under carefully controlled conditions, gave seco-taxane 27 with high diastereoselectivity for the diol moiety.

Shapiro reaction - vinyllithium - stereoselectivity - seco-taxane - taxol