Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization

Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization

A concise synthesis of two scyphostatin analogues is achieved from readily available ortho-substituted phenols. Key features include an asymmetric and biomimetic hydroxylative phenol dearomatization (HPD) reaction promoted by a chiral salen-type bis­(λ5-iodane) reagent, followed by an in situ regio-...

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Veröffentlicht in:Journal of organic chemistry 2017-11, Vol.82 (22), p.11816-11828
Hauptverfasser: El Assal, Mourad, Peixoto, Philippe A, Coffinier, Romain, Garnier, Tony, Deffieux, Denis, Miqueu, Karinne, Sotiropoulos, Jean-Marc, Pouységu, Laurent, Quideau, Stéphane
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemical synthesis
Amides - chemistry
Chemical Sciences
Iodine - chemistry
Molecular Structure
Phenols - chemistry
Pyrones - chemical synthesis
Pyrones - chemistry
Stereoisomerism
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Zusammenfassung:A concise synthesis of two scyphostatin analogues is achieved from readily available ortho-substituted phenols. Key features include an asymmetric and biomimetic hydroxylative phenol dearomatization (HPD) reaction promoted by a chiral salen-type bis­(λ5-iodane) reagent, followed by an in situ regio- and diastereocontrolled epoxidation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02366