Total Synthesis of the Novel Coenzyme Methoxatin

Article abstract of DOI:10.1021/jo00210a024

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 methylotropic 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 some elaboration of the chemistry of the unusual pyrroloquinoline heterocycle.The overall yield is ca. 15 percent in 11 operations.