Journal of the American Chemical Society · 2009 · 67 citations · 17 references
Natural SciencesChemistryMedicinal ChemistryNatural Product BiosynthesisOrganic ChemistrySynthetic Medicinal ChemistryMarine Bioactive CompoundsMarine Natural Product BiosynthesisMarine Natural ProductsMicrotubule-targeting AgentsRetrosynthetic AnalysisAldol AdditionAldol CondensationAldol ReactionMarine Natural Product DiscoveryMulti-step SynthesisNatural Product SynthesisStereoselective Aldol ReactionsSynthetic Microtubule-targeting Agents
A convergent synthesis of the marine natural product (+)-peloruside has been reported. This target has been assembled through the successive application of two methyl ketone boron aldol addition reactions to the latent C(7)-C(11) dialdehyde synthon. This approach afforded a 22-step synthesis of this natural product. The influence of resident stereocenters on aldol reaction diastereoselection has been examined in detail.
17
Peloruside A, a novel antimitotic agent with paclitaxel-like microtubule- stabilizing activity.
Kylie Hood, Lyndon M. West, Berber Rouwé et al. · PubMed · 2002 · 256 citations