Journal of the Chemical Society Perkin Transactions 1 · 1994 · 47 citations · 11 references
PharmacyChemistryMedicinal ChemistryNatural Product BiosynthesisOrganic ChemistrySynthetic Medicinal ChemistryNatural Product Drug DiscoveryRetrosynthetic AnalysisGlycoside Natural ProductsHeterocyclic Natural ProductsNatural Product SynthesisNatural Product Total SynthesisPalladium CatalystsPalladium-catalyzed Cross-couplingTotal Synthesis-derived Analogues
A total synthesis of the natural products, solamin 1 and reticulatacin 2 is described. The monotetrahydrofuran moiety 12a of compounds 1 and 2 was constructed by an eight-step reaction sequence, starting from (–)-muricatacin 5, an acetogenin derivative. The γ-lactone moieties 26 and 27 of compounds 1 and 2 were prepared by a multi-stage procedure, starting from (S)-(–)-ethyl lactate. A palladium-catalysed cross coupling reaction of compound 12a with either compound 26 or compound 27 gave the products 28 and 29 which by a three-step sequence were converted into compounds 1 and 2 respectively. Similarly, 15, 16-di-epi-solamin 3 and 17, 18-di-epi-reticulatacin 4 were synthesized.
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