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Issue 31, 2014
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Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach

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Abstract

A simple and novel synthesis of (+)-monocerin was achieved in 15 steps and 15.5% overall yield from 3-buten-1-ol employing hydrolytic kinetic resolution, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation–cyclization as the key steps.

Graphical abstract: Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach

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Publication details

The article was received on 09 May 2014, accepted on 29 May 2014 and first published on 29 May 2014


Article type: Paper
DOI: 10.1039/C4OB00965G
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Org. Biomol. Chem., 2014,12, 5973-5980

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    Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach

    U. Nookaraju, E. Begari and P. Kumar, Org. Biomol. Chem., 2014, 12, 5973
    DOI: 10.1039/C4OB00965G

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