Enantioselective synthesis of (+)‐(S)‐laudanosine and (-)‐(S)‐xylopinine
Abstract: The study presents a new pathway for the enantioselective synthesis of benzylisoquinoline alkaloids. The key steps of the synthesis of (+)-(S)-laudanosine (1) and (-)-(S)-xylopinine (2) are a Sonogashira coupling that builds up the C1-C8a bond of the benzylisoquinoline skeleton, an intramo...
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| Main Authors: | , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
20 June 2005
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| In: |
European journal of organic chemistry
Year: 2005, Issue: 13, Pages: 2689-2693 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200500095 |
| Online Access: | Verlag, Pay-per-use, Volltext: http://dx.doi.org/10.1002/ejoc.200500095 Verlag, Pay-per-use, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200500095 
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| Author Notes: | Didin Mujahidin and Sven Doye |
| Summary: | Abstract: The study presents a new pathway for the enantioselective synthesis of benzylisoquinoline alkaloids. The key steps of the synthesis of (+)-(S)-laudanosine (1) and (-)-(S)-xylopinine (2) are a Sonogashira coupling that builds up the C1-C8a bond of the benzylisoquinoline skeleton, an intramolecular Ti-catalyzed hydroamination of an alkyne, and a subsequent enantioselective imine reduction according to Noyori's protocol. |
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| Item Description: | Gesehen am 21.03.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200500095 |