Use of the Potassium Ion as a Template for the Selective Derivatization of the Antibiotic X-206

The templating effect of potassium ions on the ionophore antibiotic X-206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) position. The mechanism of acylation at C(22) w...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 64; no. 17; pp. 6252 - 6256
Main Authors O'Sulliva, Anthony C, Struber, Fritz, Ley, Steven V
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.08.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
IONOPHORE
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Summary:The templating effect of potassium ions on the ionophore antibiotic X-206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) position. The mechanism of acylation at C(22) was investigated and the aquired knowledge used to achieve selective reactions on the benzyl ester 8 using a similar metal template protection.
Bibliography:istex:15D4704BA9CA78E8A775E2FF788FA6657288529D
ark:/67375/TPS-JZPHF8L7-9
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9903151