|Title||Synthesis of a P-Glycoprotein Inhibitor and Its High-Energy ()-Isomer by Carbenoid Eliminative Cross-Coupling.|
|Publication Type||Journal Article|
|Year of Publication||2020|
|Authors||Tanpure SD, El-Mansy MF, Blakemore PR|
|Date Published||2020 04 17|
|Keywords||Alkenes, ATP Binding Cassette Transporter, Subfamily B, Member 1, Molecular Structure, Stereoisomerism|
To gauge the feasibility of carbenoid eliminative cross-coupling for the synthesis of polyfunctional alkenes, a P-glycoprotein inhibitor containing an ()-configured 4-chromanylidene-type trisubstituted olefin was prepared as well as its previously undescribed ()-isomer. Stereospecific alkene synthesis required generation of functionalized enantioenriched α-metalated carbamates [RRCM(OCN-Pr), M = Li or Bneo], and problems associated with incorrect lithiation regioselectivity and unexpected organolithium configurational lability were encountered. Solutions to these difficulties are described together with a method for ee determination of α-carbamoyloxyboronates.
|Alternate Journal||Org Lett|