title: Chemoenzymatic routes to polyoxygenated cyclooctenones related to the Eastern hemisphere of the macrolactam tripartilactam.
abstract: 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.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200 (Australia).
authors.forename: Yen
authors.initials: Y
authors.lastname: Vo
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry*; D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003503:Cyclobutanes; D034242:Cyclooctanes; D007769:Lactams; C572276:tripartilactam
keywords: cis-1,2-dihydrocatechol; cyclooctenone; enzyme catalysis; metathesis; tripartilactam