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Stereoselective Total Synthesis of the Natural (+)-Lasonolide A
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2004
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Thermodynamic Benzylidene FormationMedicinal Chemistry20-Membered MacrolactoneHeterocyclicStereoselective Total SynthesisNatural SciencesOrganic ChemistryStereoselective SynthesisChemistryHeterocycle ChemistryPharmacologyAnti-tumor AgentSynthetic ChemistryEnantioselective SynthesisNatural Product Synthesis
The natural (+)-lasonolide A (1), an anti-tumor agent, has been synthesized via thermodynamic benzylidene formation at the C22 quaternary chiral center, use of a disulfone equivalent for elongation of the C15-C17 three-carbon chain as well as introduction of the two trans olefins at C15 and C17, iodocyclization for the upper THP, Michael addition for the bottom THP, and intramolecular Horner-Emmons olefination for the 20-membered macrolactone.