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Published on: February 7, 2019
A stereoselective synthesis of the C9-C19 subunit of (+)-peloruside A
Sadagopan Raghavan1, V Vinoth Kumar
1Division of Natural Product Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India. sraghavan@iict.res.in
Abstract:
The stereoselective synthesis of a C9-C19 fragment of the potent antitumor agent peloruside A is disclosed. The C11 stereogenic centre was created by a vinylogous Mukaiyama aldol reaction following Carreira's protocol, with excellent stereocontrol. The C13 stereogenic centre was introduced by a substrate controlled reduction. The C15 stereocentre was fashioned using Noyori's asymmetric transfer hydrogenation while the Z-trisubstituted double bond was formed by a regioselective hydrostannation of an alkyne followed by methylation of the resultant vinyl stannane using Lipshutz's protocol. The C18 chiral centre was introduced by a chemoenzymatic route.
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