Total synthesis of (−)-8-epi-chromazonarol enabled by a unique N2H4·H2O promoted intramolecular oxa-Michael cyclization reaction

Total synthesis of (−)-8-epi-chromazonarol enabled by a unique N2H4·H2O promoted intramolecular oxa-Michael cyclization reaction

An enantioselective total synthesis of the natural chroman-sesquiterpenoid (−)-8-epi-chromazonarol has been accomplished by a unique N2H4·H2O promoted highly diastereo-selective oxa-Michael cyclization to construct the central chroman framework and assemble the unusual C8 stereocenter. The other sal...

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Veröffentlicht in:Organic chemistry frontiers an international journal of organic chemistry 2018-10, Vol.5 (20), p.3013-3017
Hauptverfasser: Liu, Lin, Song, Huayue, Chen, Peng, Yuan, Ziyun, Feng, Shangbiao, Zhang, Weiwei, Bowen, Fang, Xie, Xingang, She, Xuegong
Format: Artikel
Sprache:eng
Schlagworte:
Aromatic compounds
Carbonyls
Chemical reactions
Chemical synthesis
Cross coupling
Crystallography
Enantiomers
Organic chemistry
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Zusammenfassung:An enantioselective total synthesis of the natural chroman-sesquiterpenoid (−)-8-epi-chromazonarol has been accomplished by a unique N2H4·H2O promoted highly diastereo-selective oxa-Michael cyclization to construct the central chroman framework and assemble the unusual C8 stereocenter. The other salient feature of the reported synthesis involves a Stille carbonylative cross-coupling reaction to link the aryl stannane 9 and bicyclic triflate 10.
ISSN:2052-4110
2052-4110
DOI:10.1039/c8qo00901e