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Studies on the total synthesis of rifamycin. A method for the closure of the macrocyclic unit

✍ Scribed by E.J. Corey; David A. Clark

Publisher
Elsevier Science
Year
1980
Tongue
French
Weight
204 KB
Volume
21
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 under base under a complication an approach for the stereocontrolled synthesis of the C(19) to Cc271 segment of the ansa bridge and a method for stereospecific chain extension to form the 22,4g-dienoyl unit corresponding to C(15) to 3 C( 19). Another of the problems to be surmounted by any synthetic attempt, the formation of the macrocyclic unit of 1, has recently been studied and solved. These results which represent another 4 major simplification of the synthetic task are described herein.

πŸ“œ SIMILAR VOLUMES

Studies on the total synthesis of rifamy
Studies on the total synthesis of rifamycin. Highly stereoselective synthesis of intermediates for construction of the C(15) to C(29) chain
✍ E.J. Corey; Tapio Hase πŸ“‚ Article πŸ“… 1979 πŸ› Elsevier Science 🌐 French βš– 235 KB

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

A model study for the biomimetic-type sy
A model study for the biomimetic-type synthesis of rifamycin S
✍ Hideo Iio; Hiroto Nagaoka; Yoshito Kishi πŸ“‚ Article πŸ“… 1981 πŸ› Elsevier Science 🌐 French βš– 231 KB

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\_)