Asymmetric synthesis of (+)-polyanthellin A.
A concise and convergent route to (+)-polyanthellin A is presented. This synthesis features a diastereoselective cyclopropane/aldehyde [3+2] cycloaddition to install the hydroisobenzofuran core. The use of MADNTf(2) as a potent, bulky Lewis acid was essential to allow a labile beta-silyloxy aldehyde to be used in the cycloaddition. Other key steps include a ring-closing metathesis and a selective olefin oxidation.
Campbell
Matthew J
MJ
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Johnson
Jeffrey S
JS
D000447:Aldehydes / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000447:Aldehydes; D003521:Cyclopropanes; D004224:Diterpenes; D005663:Furans; C476739:polyanthellin A; C018674:tetrahydrofuran; C030797:cyclopropane