Total Synthesis of Antibiotic Karnamicin B1. -The reaction of the furan derivative (I) with bromine in MeOH gives a bromo-methoxyfuran (III) instead of the normal dimethoxyfuran. Successful ring-transformation into the trihydroxy pyridine derivative (V) provides the base for the first total synthes
Total synthesis of antibiotic karnamicin B1
β Scribed by Kazuyuki Umemura; Koichi Watanabe; Kazumasa Ono; Masanori Yamaura; Juji Yoshimura
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 177 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
The novel antifungal karnamicin B, (1), 5-hydroxy-3,4-dimethoxy-2-(2-(4-oxopentyl)-4-thiazolyl}pyridine-6-carboxamide was first synthesized via the formation of partially methylated trihydroxy pyridine by ring-transformation from the corresponding furan derivative and subsequent regioselective introduction of 2,6substituents using Meisenheimer-type reaction.
π SIMILAR VOLUMES
This communication describes the first total synthesis of asterriquinone B 1, a representative member of a group of anti-tumor metabolites of Aspergillus terreus. The synthesis described herein is potentially applicable to other members of the asterriquinone family.
Antibiotic althiomycin was totally synthesized from D-cysteine via the procedures of the coupling with sodium salt of pyrrolinone, hydroxymethylation, and the coupling with the thiazole part, successively.