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Updated: Jul 15, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Formal total synthesis of (-)-apicularen a by a strategy based on ring-closing metathesis and transannular
Young-Hee Jung1, Young-Ju Kim, Jieun Lee
1Department of Chemistry and Center for Bioactive Molecular Hybrids, Institute for NanoBio Molecular Assemblies (BK21), Yonsei University, Seoul 120-749, Korea.
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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