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Issue 17, 2013
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A stereoselective synthesis of the C9–C19 subunit of (+)-peloruside A

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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.

Graphical abstract: A stereoselective synthesis of the C9–C19 subunit of (+)-peloruside A

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Publication details

The article was received on 28 Dec 2012, accepted on 18 Feb 2013 and first published on 19 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB27508F
Citation: Org. Biomol. Chem., 2013,11, 2847-2858
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    A stereoselective synthesis of the C9–C19 subunit of (+)-peloruside A

    S. Raghavan and V. Vinoth Kumar, Org. Biomol. Chem., 2013, 11, 2847
    DOI: 10.1039/C3OB27508F

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