Chemoenzymatic routes to polyoxygenated cyclooctenones related to the eastern hemisphere of the macrolactam tripartilactam

Polyoxygenated cyclooctenones closely related to the enantiomeric form of the Eastern hemisphere of the structurally and biogenetically unusual macrolactam tripartilactam have been assembled from an enzymatically-derived and homochiral cis-1,2-dihydrocatechol. Key steps include the oxidative cleavage of the chlorinated double bond within a derivative of the starting cis-1,2-dihydrocatechol and a ring-closing metathesis reaction to establish the required eight-membered ring.