Publication | Closed Access
Sulfanyl Radical-Induced Cyclization of Linalyl Acetate to the Iridane Skeleton: A Short Synthesis of (±)-Dehydroiridomyrmecin
12
Citations
0
References
2005
Year
BiosynthesisBioorganic ChemistryDerivativesBiochemistryIridane SkeletonNatural SciencesEngineeringDiversity-oriented SynthesisSulfanyl Radical-induced CyclizationDifferent Sulfanyl RadicalsRadical (Chemistry)Sulfanyl RadicalsOrganic ChemistryLinalyl AcetatePharmacologySynthetic ChemistryEnantioselective SynthesisNatural Product Synthesis
Sulfanyl radicals promote radical cyclization both in linalyl acetate (2) and its derivative 3, leading highly selectively to monoterpenoids with an iridane skeleton. We have investigated the addition of different sulfanyl radicals such as PhS• , 4-NO2C6H4S• and PhCH2CH2S• and found that the latter radical produces the best results (87-93%). Natural iridoid dehydroiridomyrmecin (1) at an overall yield of 28% was synthesized in four steps using this method.