Rearrangement of a cyclohexyl radical to a cyclopentylmethyl radical on the avermectin skeleton |
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Authors: | Kessabi Fiona Murphy Winkler Tammo Luft Jennifer A R Houk K N |
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Institution: | Syngenta Crop Protection AG, Basel, Switzerland. fiona.murphy_kessabi@syngenta.com |
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Abstract: | The rearrangement of a substituted cyclohexyl radical to a cyclopentylmethyl radical on the skeleton of avermectin B1 was observed experimentally and explored computationally. The Stork-Nishiyama methodology was applied to the macrocycle of interest followed by a Tamao oxidation. The expected 5-6 fused ring product was observed in minor amounts. The major product was a 5-5 fused ring resulting from apparent conversion of the initially formed cyclohexyl radical to a cyclopentylmethyl radical. Preliminary computational results indicate that substituents in the macrocycle induce the rearrangement. |
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