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
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo00209a017