Total synthesis of the novel coenyzme methoxatin

JB Hendrickson, JG De Vries

Index: Hendrickson, James B.; Vries, Johannes G., de Journal of Organic Chemistry, 1985 , vol. 50, # 10 p. 1688 - 1695

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Citation Number: 22

Abstract

A convergent total synthesis of the novel coenzyme methoxatin (1) is described. This coenzyme is a pyrroloquinoline quinone tailored for efficient oxidation of methanol and formaldehyde in methylotrophic bacteria. The synthesis was achieved by joining pyrrole subunit 5a with uvitonic acid ester 8b followed by photocyclization of the resulting olefin 9 to deoxymethoxatin 10. Conversion of 10 to methoxatin proceeded in five steps and led to ...