Journal of the American Chemical Society · 2008 · 41 citations · 15 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryDiversity-oriented SynthesisHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsMacrocycle SynthesisOrganic SynthesisMacrocycle DiversificationMacrocycle Library SynthesisMacrocyclic Library ConstructionMacrocyclic Library SynthesisRing-forming ReactionsStereocontrolled Library SynthesisStereoselective MacrocyclizationTotal Synthesis-derived Analogues
The syntheses of haterumalides NA and NC were accomplished via the macrocyclization of a chlorovinylidene chromium carbenoid onto a pendant aldehyde to generate the C8-C9 bond with the desired stereoisomer as the major product. Utilizing the latter chemistry enables access to both C9 hydroxylated (haterumalides NC and ND) and C9 deoxygenated forms (haterumalides NA, NB, and NE; via deoxygenation of the C9-hydroxyl).
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