A synthesis of pseudoconhydrine and its epimer via hydroformylation and dihydroxylation
A synthesis of the alkaloid pseudoconhydrine and its epimer has been achieved using tandem hydroformylation-condensation to form the six-membered ring and stereoselective dihydroxylation to introduce oxygenation. The stereoselectivity of dihydroxylation can be explained by lipophilic and electrostat...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
19 July 2011
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| In: |
The journal of organic chemistry
Year: 2011, Volume: 76, Issue: 16, Pages: 6844-6848 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo2008912 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/jo2008912
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| Author Notes: | Roderick W. Bates, K. Sivarajan and Bernd F. Straub |
| Summary: | A synthesis of the alkaloid pseudoconhydrine and its epimer has been achieved using tandem hydroformylation-condensation to form the six-membered ring and stereoselective dihydroxylation to introduce oxygenation. The stereoselectivity of dihydroxylation can be explained by lipophilic and electrostatic effects, supported by DFT calculations. The alkaloids can be obtained either by regioselective dehydroxylation or by rearrangement, followed by reduction. |
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| Item Description: | Gesehen am 02.03.2022 |
| Physical Description: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo2008912 |