Concise syntheses of cystothiazoles A, C, D, and melithiazol B

Chem Pharm Bull (Tokyo). 2007 Nov;55(11):1610-4. doi: 10.1248/cpb.55.1610.

Abstract

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).

MeSH terms

  • Acrylates / chemical synthesis*
  • Aldehydes / chemistry
  • Anti-Bacterial Agents / chemical synthesis*
  • Antifungal Agents / chemical synthesis*
  • Models, Chemical
  • Thiazoles / chemical synthesis*

Substances

  • Acrylates
  • Aldehydes
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Thiazoles
  • cystothiazole A
  • cystothiazole C
  • cystothiazole D
  • melithiazol B