101330-11-4Relevant articles and documents
Vinyl isocyanates in alkaloid synthesis. Camptothecin model studies
Rigby, James H.,Danca, Diana M.
, p. 4969 - 4972 (1997)
Model studies directed toward camptothecin employing a vinyl isocyanateenamine cyclocondensation as the key synthetic step are reported.
Methods and intermediates for the assymmetric synthesis of camptothecin and camptothecin analogs
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, (2008/06/13)
Processes for making compounds of Formulae XIV, XV, and XVII STR1 wherein R6 is lower alkyl, R7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R8 is a moiety of Formula XVIII STR2 wherein n is 1, 2, or 3, R11 is C1 -C4 alkyl and R12 is the same as R11, or R11 and R12 together form cyclopentane or cyclohexane, and R13 is: (a) phenyl substituted 1 to 5 times with C3 -C7 secondary alkyl or C4 -C7 tertiary alkyl, or (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C3 -C7 secondary alkyl or C4 -C7 tertiary alkyl groups, R10 is C6 -C10 alkyl, aryl or alkyl aryl, and Y is H, F or Cl, are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.
Intermediates and method of making camptothecin and camptothecin analogs
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, (2008/06/13)
Compounds of Formula I STR1 are made in accordance with the following scheme: STR2 wherein R may be loweralkyl; R1 may be H, loweralkyl, loweralkoxy, or halo; R2, R3, R4, and R5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.
Is Halogen-Lithium Exchange Intramolecularly Competitive with Removal of an Acidic Hydrogen? Reinvestigation of a Recent Claim
Gallagher, Donald J.,Beak, Peter
, p. 7984 - 7987 (2007/10/02)
A careful reinvestigation of a recent report in which the iodine-lithium exchanges of 2-iodo-3-(deuterioxymethyl)quinoline (1) and 2-iodo-3-(hydroxymethyl)quinoline (4) are interpreted to have occurred prior to abstraction of the alcoholic hydrogen has been carried out. Accurate analyses of the reaction products by FI mass spectrometry give results that are different from those recently reported and are consistent with a mechanism in which removal of the acidic hydrogen takes place prior to iodine-lithium exchange on a molecular scale. The interpretation that suggested the opposite sequence was based on deuterium incorporation values that appear to be inaccurate due to the limitations of the 1H NMR methods used.
Evidence in favor of lithium-halogen exchange being faster than lithium-acidic hydrogen (deuterium) exchange
Narasimhan, Nurani S.,Sunder, Nurani M.,Ammanamanchi, Radhakrishna,Bonde, Bhagavat D.
, p. 4431 - 4435 (2007/10/02)
Treatment of 2-iodo-3-(deuterioxymethyl)quinoline with 1.5 equiv of n-butyllithium in ether, followed by aqueous work up, furnished 2-deuterio-3-(hydroxymethyl)quinoline in greater than 50% yield, confirming our earlier report,2 which has been
