Chemoenzymatic Synthesis of Natural Products and …

Probably the winner for the gassiest sequence described is from a Movassaghi paper that I remember from last year. Although the reaction hasn't actually been used to make a natural product yet, it looks like a useful way to access hetero cyclotryptamine natural products, of which there are many. The idea is to synthesise an unsymmetrical sulfamide, where the two amines are connected to the two units to be linked. Oxidation of this with NCS then generated a thiadiaziridine dioxide in some bizarre Aza-Myers-Ramberg-Bäcklund-type reaction. This then lost sulfur dioxide as expected to give a diazene that was decomposed photolytically with loss of nitrogen to give a pair of radicals that recombined quickly. Amazingly this recombination occurred sufficiently to prevent the formation of homodimeric products. Neat reaction - I love the fact that the linker is completely traceless!

Research Synopsis: Total synthesis of natural products and the development of new synthetic methods

Graduate students in organic chemistry of natural products take a one-year course sequence in mechanistic organic chemistry and another in synthetic organic chemistry. Additionally, one-semester courses are required in advanced physical chemistry and the organic chemistry of natural products.


Asymmetric Synthesis of Drugs and Natural Products - …

Research Synopsis: Synthesis, catalysis and chemical biology of organic molecules. Chemistry of functional polymers of both non-biological and biological nature.