Organic Letters · 2005 · 65 citations · 45 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisAbsolute Configuration AssignmentAbsolute Configuration DeterminationEnantioselective SynthesisNatural Product Total SynthesisNegishi CouplingRing-forming ReactionsSix-membered Heterocycles
[reaction: see text] The first enantioselective synthesis of (+)-trans-195A is described. The structure has been constructed by ring-rearrangement metathesis (RRM) and zirconium-mediated Negishi-coupling, used for the first time to prepare 6,6-membered heterocycles, as key steps. By comparison of the synthesized material with the isolated natural product, the absolute configuration of natural trans-195A was determined to be (2R,4aS,5R,8aS)-(-).
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