Synthetic studies of rifamycins. VI. Preparation and elaboration of the aromatic segment for the synthesis of rifamycin W
โ Scribed by Masaya Nakata; Mitsuhiro Kinoshita; Shigeru Ohba; Yoshihiko Saito
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 269 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
Acid treatment of the hydroperoxide 5 yielded the enol ether 9. Hydrogenation of 9 gave the dihydro derivative, the structure of which was established by comparisonwith the substance synthesized by a different route. White, Martinelli, and Lancini have succeeded in the isolation of rifamycin W (l\_)
The formation of the macro ring of rifamycin S (4) has been accomplished by generating the lactam linkage through cyclization of a suitably protected and activated amino acid (4). 1 Previous papers from these laboratories on the synthesis of rifamycin S (1) have dealt with 2 in 80% yield occurs unde
One interesting possibility for the elaboration of the C(15) to C(29) chain of the antibiotic rifamycin S (l)l is illustrated by the antithetic relationship indicated in Scheme I. In this plan the ry SCHEME I 3 intermediate zwhich corresponds to the C(19) to C(27) chain is disconnected to a bifuncti