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Wadsworth-Emmons-Horner homologation

The final steps of the synthesis are summarized in Scheme 34. After a sequence of protection-reduction-oxydation, 171 was transformed to aldehyde 172 which was directly submitted to a Horner-Wadsworth-Emmons homologation with the requisite stabilized reagent K under Ando conditions [115] to give the corresponding a,(3-unsaturated ester 173 (Z/E > 95/5) in 84% yield. Treatment of ester 173 with 1% HC1, EtOH led to (-)-pironetin after purification (89% yield). [Pg.46]

An efficient access to (Z)-/l-fluoroallyl alcohols (382), based on the two carbon homologation of aromatic aldehydes by the Horner-Wadsworth-Emmons reaction with 2-(diethoxyphosphoryl)-2-fluoro-ethanethioic acid S-ethyl ester (381), followed by reduction with sodium borohydride, has been devepoped by Rolando and co-workers (Scheme 134). ... [Pg.306]

See other pages where Wadsworth-Emmons-Horner homologation is mentioned: [Pg.430]    [Pg.430]    [Pg.403]    [Pg.1484]    [Pg.98]    [Pg.100]    [Pg.259]    [Pg.521]   
See also in sourсe #XX -- [ Pg.430 ]



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