Total synthesis of ionophore antibiotic X-14547A

Total synthesis of ionophore antibiotic X-14547A

A hishly stereocontrolled and convergent total synthesis of optically active ionophore antibiotic X-14547A was designed and carried out. Degradative reactions led to the key intermediates 3 and 6, which served as convenient comparison stages. Attachment of the 2-ketopyrrole system by new technology...

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Veröffentlicht in:Journal of organic chemistry 1985-05, Vol.50 (9), p.1440-1456
Hauptverfasser: Nicolaou, K. C, Papahatjis, D. P, Claremon, D. A, Magolda, R. L, Dolle, R. E
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Sprache:eng
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Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
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container_end_page 1456
container_issue 9
container_start_page 1440
container_title Journal of organic chemistry
container_volume 50
creator Nicolaou, K. C
Papahatjis, D. P
Claremon, D. A
Magolda, R. L
Dolle, R. E
description A hishly stereocontrolled and convergent total synthesis of optically active ionophore antibiotic X-14547A was designed and carried out. Degradative reactions led to the key intermediates 3 and 6, which served as convenient comparison stages. Attachment of the 2-ketopyrrole system by new technology involving the 2-pyridinethiol ester functionality and a magnesium-pyrrole reagent proceeded smoothly and after base hydrolysis completed the total synthesis of X-14547A.
doi_str_mv 10.1021/jo00209a017
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source American Chemical Society Journals
subjects Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
title Total synthesis of ionophore antibiotic X-14547A
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