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15th November 2014 @ 22:05

OSM is now lucky enough to include chemists from Sydney Grammar School, who are making some much-needed molecules in Series 4. Alice already welcomed them on board here and here. Our intrepid explorers are Jason Chami, Evan Hockings, William Talbot, Sebastian Schwartz, Hugh Russell, James Kalas, James Manton-Hall, Andreas Orsmond, Mackenzie Shaw and Alex Su (ping @O_S_M if we've missed anyone, guys) They are working together, and the relevant reactions have codes with “SGS” in them.

These guys are making an important synthetic intermediate, shown below right, which can be used in a subsequent reaction to deliver new candidate antimalarials. This is a "divergent" pathway, since we can attach various groups to the Sydney Grammar compound to make a variety of molecules with the same chemistry.

Sydney Grammar School Target

The chemistry’s not easy, but with some precedent this year from Jo Ubels and Tom MacDonald, and inspiration and guidance from Alice Williamson, and expert tuition from their teachers Erin Sheridan and Trent Wallis, they should have a shot at this tricky chemistry. (If you're a student reading this and asking "Can I input?" the answer is "yes" - get in touch)

The route being pursued is nicely shown here, where the first step (SGS 1-1) is also described. The second step (SGS 2-1) was a condensation of a hydrazine with para-CN benzaldehyde, and an attempt was made in parallel using a pyridine aldehyde (SGS 3-1). As this chemistry grows, we're going to need to add it to the synthesis section of the wiki, as a summary of progress.

The chemistry’s not easy - this is certainly more difficult than the stuff that I was doing in high school. Great start, guys - we’re all rooting for you to be able to get to the end of the synthetic sequence! These molecules will be very useful, right now.

 

This post originally authored by Mat Todd


Strings for Google

ClC1=CN=CC(Cl)=N1 InChI=1S/C4H2Cl2N2/c5-3-1-7-2-4(6)8-3/h1-2H LSEAAPGIZCDEEH-UHFFFAOYSA-N

ClC1=CN=CC2=NN=C([Ar])N21 InChI=1S/C5H2ArClN4/c6-5-10-9-4-2-8-1-3(7)11(4)5/h1-2H JTBLVZJIEUOKIG-UHFFFAOYSA-N




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Sydney Grammar Target.png
Sydney Grammar Target.cdxml