title: Formal total synthesis of (-)-apicularen a by a strategy based on ring-closing metathesis and transannular cyclization.
abstract: A formal synthesis of (-)-apicularen A, a potent antitumor agent with unique biological properties, has been completed in a 15-step sequence starting from a known, enantiomerically pure hydroxyepoxide, which was generated by using the Jacobsen hydrolytic-kinetic-resolution methodology. The 12-membered macrocyclic lactone in the target was constructed by ring-closing metathesis, and the trans-tetrahydropyran ring system was created through the transannular etherification of a hydroxyalkene.
authors.affiliation: Department of Chemistry and Center for Bioactive Molecular Hybrids, Institute for NanoBio Molecular Assemblies (BK21), Yonsei University, Seoul 120-749, Korea.
authors.forename: Young-Hee
authors.initials: YH
authors.lastname: Jung
authors.forename: Young-Ju
authors.initials: YJ
authors.lastname: Kim
authors.forename: Jieun
authors.initials: J
authors.lastname: Lee
authors.forename: Jinsung
authors.initials: J
authors.lastname: Tae
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006868:Hydrolysis; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; C117813:apicularen A