Synthesis of (+)-goniothalamin and its enantiomer by combination of lipase catalyzed resolution and alkene metathesis |
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| Authors: | Eirik Sundby Thorleif Anthonsen Arne Jørgen Aasen |
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| Institution: | a Department of Chemistry, Norwegian University of Science and Technology, N-7491 Trondheim, Norway
b Department of Medicinal Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, N-0316 Blindern, Oslo, Norway |
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| Abstract: | (+)-Goniothalamin has been synthesized by lipase catalyzed resolution of (1E)-1-phenylhexa-1,5-dien-3-ol using vinyl acrylate as acyl donor followed by ring closing metathesis of the formed (1R)-1-(E)-2-phenylvinyl]but-3-enyl acrylate. The unreacted alcohol from the resolution, (1E,3S)-1-phenylhexa-1,5-dien-3-ol, was esterified non-enzymatically, and used for synthesis of (−)-goniothalamin. |
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| Keywords: | (+)-Goniothalamin (&minus )-Goniothalamin Candida antarctica lipase B Resolution Alkene metathesis Grubbs' catalyst |
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