Enantioselective modular synthesis of cyclohexenones: total syntheses of (+)-crypto- and (+)-cnfectocaryone
A modular synthesis of cyclohexenones is described and applied to the first enantioselective total syntheses of (+)-crypto- and (+)-infectocaryone. Key steps in the synthesis of cyclohexenones are an iridium-catalyzed allylic alkylation, nucleophilic allylation, and ring-closing metathesis. On the w...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
August 02, 2010
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| In: |
Organic letters
Year: 2010, Volume: 12, Issue: 17, Pages: 3886-3889 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/ol101588j |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/ol101588j
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| Author Notes: | Géraldine Franck, Kerstin Brödner, Günter Helmchen |
| Summary: | A modular synthesis of cyclohexenones is described and applied to the first enantioselective total syntheses of (+)-crypto- and (+)-infectocaryone. Key steps in the synthesis of cyclohexenones are an iridium-catalyzed allylic alkylation, nucleophilic allylation, and ring-closing metathesis. On the way to (+)-cryptocaryone, a catch and release strategy involving an iodolactonization/elimination and a regioselective C-acylation were used. |
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| Item Description: | Gesehen am 07.11.2023 |
| Physical Description: | Online Resource |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/ol101588j |