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-member...

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Bibliographic Details
Published inChemistry, an Asian journal Vol. 2; no. 5; p. 656
Main Authors Jung, Young-Hee, Kim, Young-Ju, Lee, Jieun, Tae, Jinsung
Format Journal Article
LanguageEnglish
Published Germany 04.05.2007
Subjects
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Cyclization
Hydrolysis
Kinetics
Magnetic Resonance Spectroscopy
Mass Spectrometry
Stereoisomerism
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Summary: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.
ISSN:1861-471X
DOI:10.1002/asia.200700024