Article

Formal total synthesis of (-)-apicularen a by a strategy based on ring-closing metathesis and transannular cyclization.

Department of Chemistry and Center for Bioactive Molecular Hybrids, Institute for NanoBio Molecular Assemblies (BK21), Yonsei University, Seoul 120-749, Korea.
Chemistry - An Asian Journal (impact factor: 4.5). 06/2007; 2(5):656-61. DOI:10.1002/asia.200700024 pp.656-61
Source: PubMed

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.

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Keywords

12-membered macrocyclic lactone
 
hydroxyalkene
 
Jacobsen hydrolytic-kinetic-resolution methodology
 
ring-closing metathesis
 
trans-tetrahydropyran ring system
 

Young-Hee Jung