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Studies on the total synthesis of rifamycin. Highly stereoselective synthesis of intermediates for construction of the C(15) to C(29) chain

✍ Scribed by E.J. Corey; Tapio Hase

Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 235 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85964-5

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✦ Synopsis

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 bifunctional nucleophilic carbonyl equivalent (4) and two fragments, 2 and 5 which, except for terminal functional group differentiation, a# are antipodal. In principle 2 and2might be synthesized economically from enantiomeric but otherwise identical 6-carbon precursors.

This note presents a solution to the problem of synthesis of 2 and 5 in an efficient and highly stereoselective way which was developed in these Laboratories in the period 1974 -1975.

Although it was our intention to defer publication until synthesis of the complete C(15) to C(29) chain was accomplished, the recent appearance2 of a related study prompts disclosure of our results at this time. 3

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