Total synthesis of (-)-deguelin via an iterative pyran-ring formation strategy

Total synthesis of (-)-deguelin via an iterative pyran-ring formation strategy

Enantioselective synthesis of (-)-deguelin was accomplished via an iterative pyran-ring formation approach. The key features involve the anionic addition of a chromene unit to aryloxy alkyl aldehyde for the double cyclization precursor and iterative pyran ring formation by Pd-catalyzed O-arylation a...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2015-05, Vol.51 (43), p.9026-9029
Hauptverfasser: Lee, Seungbeom, An, Hongchan, Chang, Dong-Jo, Jang, Jaebong, Kim, Kyeojin, Sim, Jaehoon, Lee, Jeeyeon, Suh, Young-Ger
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Catalysis
Cyclization
Formations
Palladium
Palladium - chemistry
Precursors
Pyrans - chemistry
Rotenone - analogs & derivatives
Rotenone - chemical synthesis
Rotenone - chemistry
Stereoisomerism
Strategy
Synthesis
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Zusammenfassung:Enantioselective synthesis of (-)-deguelin was accomplished via an iterative pyran-ring formation approach. The key features involve the anionic addition of a chromene unit to aryloxy alkyl aldehyde for the double cyclization precursor and iterative pyran ring formation by Pd-catalyzed O-arylation and C-arylation, respectively.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc02215k