Enantioselective synthesis of the alcohol 'arm' for the ether compounds #167

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alintheopen opened this Issue Mar 27, 2014 · 3 comments

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alintheopen commented Mar 27, 2014

Paucity of TMS-CN, lack of preparative chiral HPLC and a passion for enantioselective synthesis has led me to consider an alternative route to the alcohol side chain required for the chiral ether compounds (e.g. MMV670652).
Based on PhD work that I did with Aurélien Bigot and Matthew J Gaunt, I'm working on an catalytic enantioselective route to this side chain. Based on (http://pubs.acs.org/doi/abs/10.1021/ja206047h) and the route below:
chiral synthesis

alintheopen self-assigned this Mar 27, 2014

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alintheopen commented Apr 3, 2014

Synthesis of Iodonium Salt:
Synthesis of (3,4-difluorophenyl)(mesityl)iodonium triflate (AEW 128-1)(http://malaria.ourexperiment.org/uri/54c)

Synthesis of N-acyl-oxazolidinone:
Synthesis of 3-(2-(Benzyloxy)acetyl)oxazolidin-2-one (AEW 129-1)(http://malaria.ourexperiment.org/uri/558)

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mattodd commented Apr 4, 2014

Lovely chemistry. Freon gas?

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alintheopen commented Apr 4, 2014

yeah...no Freon! Scheme is copied and pasted from the earlier CRO route. We may not introduce CHF2 anymore but focus on other more synthetically accessible ethers instead.

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