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.
Keywords: cis-1,2-dihydrocatechol; cyclooctenone; enzyme catalysis; metathesis; tripartilactam.
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