Biomimetic syntheses of pretetramides. 1. Synthesis of pretetramide by tandem extension of a polyketide chain

SG Gilbreath, CM Harris, TM Harris

Index: Gilbreath; Harris Journal of the American Chemical Society, 1988 , vol. 110, # 18 p. 6172 - 6179

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Citation Number: 52

Abstract

Abstract: Pretetramide (4), the fully aromatic naphthacenic precursor in the biosynthesis of 6- demethyltetracycline (2), has been synthesized in biomimetic-type fashion using a [3+(2 X 2)+ 1+ 21 strategy. Tandem additions of terr-butyl acetoacetate dianion to the bis (N-methyl- N-methoxyamide)(9) of 3 4 1-pyrrolidinyl) glutaric acid followed by two spontaneous aldol cyclizations produced dihydroxynaphthalene diester 7b. Conversion of 7b to anhydride 14 ...