Concise Syntheses of Cystothiazoles A, C, D, and Melithiazol B

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概要

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• A convergent synthesis of cystothiazoles C 1 and D 3 was achieved based on Julia coupling between the functionalized aldehyde 5b, corresponding to left half of the final molecule, and aryl sulfone 6 or 7, bearing a bithiazole moiety, corresponding to right half. Methylation of 1 and 3 gave cystothiazole A 2 and melithiazol B 4, respectively. The overall yield (5 steps from (2R, 3S)-3-methylpent-4-yne-1, 2-diol 10; 57%) of 5b via the present route was improved in comparison to that of the previously reported functionalized aldehyde 5a (7 steps from 10; 13%). By applying the modified Julia coupling method, selectivity (6E/6Z=20 : 1-26 : 1) toward the (6E)-form of the coupled products (15 or 19) against the corresponding (6Z)-form was improved in comparison to the Wittig method (6E/6Z=4 : 1-6.9 : 1).

• 公益社団法人日本薬学会の論文
• 2007-11-01

著者

• AKITA Hiroyuki

  School of Pharmaceutical Science, Toho University

• Akita Hiroyuki

  School Of Pharmaceutical Sciences Toho University

• Akita Hiroyuki

  School Of Parmaceutical Sciences Toho University

• IWAKI Yuki

  Research Institute, Novartis Pharma K. K.

• Iwaki Yuki

  Research Institute Novartis Pharma K. K.:school Of Pharmaceutical Sciences Toho University

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