An expeditious synthesis of bruguierol A.
A very simple strategy for the construction of 2,3-benzofused 8-oxabicyclo[3.2.1]octane derivatives is reported. This new process is based on a platinum-catalyzed tandem intramolecular hydroalkoxylation-hydroarylation reaction of aryl-substituted pentynol derivatives. This reaction has been applied in the key step of the total synthesis of bruguierol A, allowing the synthesis of this natural product in a very straightforward manner.
Fañanás
Francisco J
FJ
Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al CSIC, Universidad de Oviedo, Julián Clavería 8, 33006-Oviedo, Spain. fjfv@uniovi.es
Fernández
Amadeo
A
Cevic
Deniz
D
Rodríguez
Félix
F
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D010984:Platinum / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D019086:Bridged Bicyclo Compounds, Heterocyclic; D006575:Heterocyclic Compounds, 3-Ring; C538743:bruguierol A; D010984:Platinum