1160714-65-7Relevant articles and documents
Construction of the 5,10b-phenanthridine skeleton using [3+2]-cycloaddition of a non-stabilized azomethine ylide: Total synthesis of (±)-maritidine and (±)-crinine alkaloids
Pandey, Ganesh,Gupta, Nishant R.,Gadre, Smita R.
, p. 740 - 750 (2011)
Vicinal quaternary and tertiary stereocenters of the 5,10b-phenanthridine skeleton 1 are constructed simultaneously in one step by the [3+2]-cycloaddition of non-stabilized azomethine ylide 9, generated by sequential double desilylation of 10 utilizing silver(I) fluoride as a one-electron oxidant. The regio- as well as stereochemical origin of this cycloaddition reaction is explained through a favorable transition state 9″. The strategy is successfully applied for the total synthesis of the biologically active alkaloids (±)-maritidine (1a), (±)-crinine (1b), and their analogues (1d, 1e, and 1f). The synthesis features construction of the BD ring with concomitant installation of a quarternary and tertiary carbon in a single operation by employing intramolecular 1,3-dipolar cycloaddition of a non-stabilizedazomethine ylide. Oxo-maritidine and oxo-crinine were found to be advanced and efficient intermediates for the synthesis of natural products of this class.
Stereoselective one-step construction of vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton: Total synthesis of (±)-maritidine
Pandey, Ganesh,Gupta, Nishant R.,Pimpalpalle, Tukaram M.
supporting information; experimental part, p. 2547 - 2550 (2009/10/18)
The challenging vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton are created in a single step utilizing intramolecular [3 + 2]-cycloaddition of nonstabilized azomethine ylide as the key step. The application of the
