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TMSI-Mediated Prins Cyclization: Diastereoselective Synthesis of 4-Iodo-2,6-Disubstituted Tetrahydropyrans and Synthesis of (±)-Centrolobine
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2005
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Enantioselective SynthesisEngineeringNatural SciencesDiversity-oriented SynthesisDiastereoselective SynthesisHomoallyl AlcoholsOrganic Chemistry4-Iodo-2,6-disubstituted TetrahydropyransStereoselective SynthesisChemistryNatural Product SynthesisSynthetic ChemistryBiomolecular EngineeringTmsi-mediated Prins CyclizationIodo PyransGood Yields
The reaction of aldehydes with homoallyl alcohols in the presence of TMSI generated in situ from TMSCl and NaI produced 4-iodo-tetrahydropyrans in good yields as a mixture of diastereoisomers, which are separated and characterized. These iodo pyrans are reported for the first time. This methodology was extended to the synthesis of (±)-centrolobine.