Tandem addition-cyclization mediated by sulfanyl radicals: a versatile strategy for iridoids synthesis |
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| Authors: | Elena M. Sá nchez |
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| Affiliation: | Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avda de Fuentenueva s/n, 18071 Granada, Spain |
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| Abstract: | Sulfanyl radicals trigger a tandem addition-cyclization protocol in linalool or citronelene derivatives for the efficient construction of the iridane monoterpene skeleton. Best results in yields and diastereoselectivity were obtained when phenylethylsulfanyl was used as radical initiator. We have proved the utility of this protocol with the enantiospecific synthesis of natural iridane dehydroiridomyrmecin starting from a (−)-linalyl acetate ester derivative in five steps with a 28% overall yield. |
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| Keywords: | Sulfanyl radical Radical cyclizations Iridanes Enantioselective synthesis |
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