Regiodivergent iodocyclizations for the highly diastereoselective synthesis of syn- and anti-hydroxyl-isochromanones and -isobenzofuranones: concise synthesis of the isochromanone core of the ajudazols
<p>An efficient synthetic strategy to access hydroxyl-isochromanone and -isobenzofurans from readily available joint alkene precursors by a regiodivergent one-pot iodocyclization-substitution tandem process is reported. The cyclizations proceed with excellent diastereoselectivities, with <i...
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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
[2016]
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| In: |
Synthesis
Year: 2015, Volume: 48, Issue: 5, Pages: 697-709 |
| ISSN: | 1437-210X |
| DOI: | 10.1055/s-0035-1561278 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1055/s-0035-1561278 Verlag, lizenzpflichtig, Volltext: http://www.thieme-connect.de/DOI/DOI?10.1055/s-0035-1561278 
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| Author Notes: | Sebastian Thiede, Peter Maria Winterscheid, Jan Hartmann, Gregor Schnakenburg, Sebastian Essig, Dirk Menche |
| Summary: | <p>An efficient synthetic strategy to access hydroxyl-isochromanone and -isobenzofurans from readily available joint alkene precursors by a regiodivergent one-pot iodocyclization-substitution tandem process is reported. The cyclizations proceed with excellent diastereoselectivities, with <i>E</i>-alkenes giving <i>syn</i>-configured products and <i>Z</i>-alkenes giving <i>anti</i>-products. A strong influence of light on the regioselectivity of the reaction was observed. High yields were also observed under radical conditions. The protective-group-free method enables a highly concise synthesis of the authentic isochromanone core of the ajudazols, which are highly potent inhibitors of the mitochondrial respiratory chain.</p> |
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| Item Description: | Published online: 29.12.2015 Gesehen am 27.05.2020 |
| Physical Description: | Online Resource |
| ISSN: | 1437-210X |
| DOI: | 10.1055/s-0035-1561278 |