A convergent synthesis of a twelve-membered macrolide natural product, (6R,12S)-6-hydroxy-12-methyl-1-oxacyclododecane-2,5-dione

Article abstract of DOI:10.1002/hlca.201200064

A new polyketide metabolite, the twelve-membered macrolide 1, isolated from the endophytic fungal strain Cladosporium tenuissimum LR 463 of Maytenus hookeri, whose structure had been determined as (6R,12S)-6-hydroxy-12-methyl-1- oxacyclododecane-2,5-dione, was synthesized for the first time by a convergent strategy via Yamaguchi esterification of 2 with 3 and ring-closing metathesis (RCM) to afford the cyclic ester 1 that was eventually transformed to the target molecule. However, the total synthesis revealed that the assigned structure of the natural product is not correct.