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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.


Hikaru Yoshimura, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama. Unified synthesis of tirandamycins and streptolydigins. Chemical communications (Cambridge, England). 2015 Dec 11;51(95):17004-7

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PMID: 26448062

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