Liebigs Annalen der Chemie

Functionally substituted vinyl carbanions, 42. Synthesis of the top half of chlorothricolide

R Hirsenkorn, RR Schmidt

Index: Hirsenkorn, Rolf; Schmidt, Richard R. Liebigs Annalen der Chemie, 1990 , # 9 p. 883 - 899

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Citation Number: 16

Abstract

Abstract β-Lithiated functionally substituted acrylates 2a–c prove to be versatile building blocks for spirotetronate syntheses useful in top half syntheses of the aglycon chlorothricolide 1 of the macrolide antibiotic chlorothricin. The electrophilic-nucleophilic cyclohexanone derivatives 27-cis/trans (with relative cis or trans relationship of the carboxylate group) required in this synthesis design are obtained via a cycloaddition route ...