Abstract: The interplay between total synthesis and methodology is a driver of innovation inorganic synthesis. Challenging bond formations in complex systems necessitate thedevelopment ever more robust new reactions, which intern can enable more efficientsyntheses. The need for powerful synthetic organic chemistry can't be understated becauseof its utility in applications such as medicine, petrochemicals, plastics, and agrichemicals.Herein, we present how total synthesis drives innovation in organic chemistryFirst, a novel cyclization reaction between pyridine and glutaryl chloride is discussedwhich has enabled the synthesis of seven lupin alkaloids. Next, the development of aconvergent fragment coupling tactic based upon the semi-pinacol rearrangement isevaluated for its generality inspired by the total synthesis of several C19 diterpenoidalkaloids. Lastly, a convergent fragment coupling approach is applied to the total synthesisof falcatin A based upon a Mukaiyama Michael tandem Mukaiyama aldol reaction.
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The racemic amine 2a (3.00 g; 10.97 mmol) is dissolved in 26 ml of MeOH at 50-65C in a flask fitted with a mechanical stirrer. Then, under continuous stirring, the amount of 4.44g (10.97 mmol) of(R,R)-di-p-toluoyl-tartaric acid monohydrate of formula (R,R)-3b is added and heating continues for another 10-15 mm. A crystallizing seed of the salt of formula (5)- 4ab is added to the resulting clear solution at the same temperature. The mixture is left to slowly cool down to the room temperature and the stirring continues overnight. The resulting crystals are aspirated, washed with icy methanol (2 x 2 ml) and dried at the room temperature.This provides 4.27 g of the product of formula (S)-4ab (yield 59%), ee 30.0% (1-IPLC).
10 mg of the racemic amine of formula 2a is weighed into a reaction vial, 100 al of the respective (methanol, ethanol, acetone, acetonitrile, ethyl acetate, toluene, chloroform, tetrahydrofuran, 2-methyltetrahydrofuran, or 1,4-dioxane, or their mixtures with water) solvent is added and the mixture is moderately heated up until all the amine of formula 2a is dissolved. Then, 0.5, or 1.0 molar equivalent of the respective resolution agent is added and the mixture is reheated to produce a clear solution. The reaction vial is closed and left to cool down to the room temperature. The formation of possible crystalline salts is monitored after 2,4, 6, 24 and after 48 hours. Possible crystalline material and mother liquors are analyzed by means of HPLC.
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