The Journal of Organic Chemistry · 2004 · 45 citations · 31 references
PharmacyChemistryMedicinal ChemistryNatural Product BiosynthesisOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisMacrocycle SynthesisOrganic SynthesisRetrosynthetic AnalysisStereochemical OptimizationAldol CondensationAldol ReactionAsymmetric Heterocycle SynthesisEster DeprotectionMacrocycle Library SynthesisMacrocyclic Library SynthesisSelective DeprotectionTotal Synthesis-derived Analogues
A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.
31
Synthesis of epothilones A and B in solid and solution phase
K. C. Nicolaou, Nicolas Winssinger, Joaquı́n Pastor et al. · Nature · 1997 · 399 citations
Total Synthesis of (−)‐Epothilone A
Dieter Schinzer, Anja Limberg, Armin Bauer et al. · Angewandte Chemie International Edition in English · 1997 · 187 citations