A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms

A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms

A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement. Get shorty:...

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Veröffentlicht in:Chemistry : a European journal 2016-08, Vol.22 (33), p.11597-11600
Hauptverfasser: Ferrara, Steven J., Burton, Jonathan W.
Format: Artikel
Sprache:eng
Schlagworte:
aphanamol
Biological Products
Catalysis
Catalysts
Chemistry
Claisen rearrangement
Communication
Communications
conjugate addition
Conjugates
Cyclization
Enantiomers
Natural products
Oxidation-Reduction
radical cyclization
Radicals
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
Synthesis
total synthesis
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Zusammenfassung:A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement. Get shorty: A short synthesis of the biologically active sesquiterpene natural product (+)‐aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring‐expanding Claisen rearrangement.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201602669