A mechanistic and synthetic study of organocopper substitution reactions with some homoallylic and cyclopropylcarbinyl substrates : Application to isoprenoid synthesis |
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| Authors: | G.H. Posner J-S. Ting C.M. Lentz |
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| Affiliation: | Department of Chemistry, The Johns Hopkins University, Baltimore, MD 21218, U.S.A. |
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| Abstract: | The double bond of cholesteryl and 5-norbornen-2-yl tosylates and the cyclopropane ring of cyclopropylmethylcarbinyl tosylate participate in organocuprate substitution reactions; retention of configuration at the nucleofugal sp3-C atom and skeletal reorganizations are observed. A plausible mechanism for these reactions is discussed. Coupling of homogeranyl iodide with a four-carbon, functionalized, vinylic cuprate reagent is applied to stereospecific synthesis of trans, trans-farnesol. |
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