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Issue 95, 2015
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Unified synthesis of tirandamycins and streptolydigins

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Abstract

The asymmetric total syntheses of tirandamycins A–D and tirandalydigin as well as the synthesis of the left-hand fragment of streptolydiginone and streptolydigin from a common intermediate are described. The comprehensive approach features the highly enantio- and diastereoselective assembly of the anti,anti,syn-stereotetrad unit which relies on a cinchona alkaloid-catalyzed asymmetric Morita–Baylis–Hillman reaction.

Graphical abstract: Unified synthesis of tirandamycins and streptolydigins

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Publication details

The article was received on 16 Sep 2015, accepted on 29 Sep 2015 and first published on 29 Sep 2015


Article type: Communication
DOI: 10.1039/C5CC07749D
Chem. Commun., 2015,51, 17004-17007

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    Unified synthesis of tirandamycins and streptolydigins

    H. Yoshimura, K. Takahashi, J. Ishihara and S. Hatakeyama, Chem. Commun., 2015, 51, 17004
    DOI: 10.1039/C5CC07749D

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