Formal total synthesis of (-)-apicularen a by a strategy based on ring-closing metathesis and transannular cyclization.
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.
Jung
Young-Hee
YH
Department of Chemistry and Center for Bioactive Molecular Hybrids, Institute for NanoBio Molecular Assemblies (BK21), Yonsei University, Seoul 120-749, Korea.
Kim
Young-Ju
YJ
Lee
Jieun
J
Tae
Jinsung
J
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
D019086:Bridged Bicyclo Compounds, Heterocyclic; C117813:apicularen A