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1.
Org Lett ; 22(8): 2999-3003, 2020 04 17.
Article in English | MEDLINE | ID: mdl-32227909

ABSTRACT

To gauge the feasibility of carbenoid eliminative cross-coupling for the synthesis of polyfunctional alkenes, a P-glycoprotein inhibitor containing an (E)-configured 4-chromanylidene-type trisubstituted olefin was prepared as well as its previously undescribed (Z)-isomer. Stereospecific alkene synthesis required generation of functionalized enantioenriched α-metalated carbamates [R1R2CM(O2CNi-Pr2), 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.


Subject(s)
Alkenes/chemical synthesis , ATP Binding Cassette Transporter, Subfamily B, Member 1/antagonists & inhibitors , Alkenes/chemistry , Alkenes/pharmacology , Molecular Structure , Stereoisomerism
2.
Org Lett ; 18(14): 3450-3, 2016 07 15.
Article in English | MEDLINE | ID: mdl-27377995

ABSTRACT

The Beckmann rearrangement of ketoximes, mediated by ammonium persulfate-dimethyl sulfoxide as a reagent, has been achieved under neutral conditions. Based on the radical trapping and (18)O-labeling experiments, the transformation follows a mechanism involving a radical pathway. The scope and generality of the developed protocol has been demonstrated by 19 examples. The developed protocol and Pd-catalyzed intramolecular double C-H activation were used as key steps in the formal total synthesis of antimalarial natural product isocryptolepine.


Subject(s)
Antimalarials/chemical synthesis , Indole Alkaloids/chemical synthesis , Quinolines/chemical synthesis , Ammonium Sulfate/chemistry , Catalysis , Dimethyl Sulfoxide/chemistry , Free Radical Scavengers/chemistry , Free Radicals/chemistry , Stereoisomerism
3.
Beilstein J Org Chem ; 11: 1008-16, 2015.
Article in English | MEDLINE | ID: mdl-26199655

ABSTRACT

Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.

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