Microwave-assisted gold(I) catalyzed pyran ring opening in brevifloralactone: synthesis of the hawtriwaic acid core

Miranda, Luis D.; Marrero, Joaquín González; Bautista, Elihú; Maldonado, Emma; Ortega, Alfredo

doi:10.1016/j.tetlet.2008.11.087

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Formation Of Carbon−oxygen Bonds1

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2009

2015

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Cited by 4 publications

(2 citation statements)

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“…In addition, a gold-catalyzed double intramolecular alkyne hydroalkoxylation was performed in order to obtain the bisbenzannelated spiroacetal core of rubromycins 268 . Finally, Miranda, Marrero, and co-workers have reported the microwave-assisted Au(I)-catalyzed cleavage of the pyran ring of brevifloralactone to form an acetal which, after oxidation, gives access to the hawtriwaic acid ( 269 ) core.…”

Section: Formation Of Carbon−oxygen Bondsmentioning

confidence: 99%

Gold-Catalyzed Carbon−Heteroatom Bond-Forming Reactions

2011

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Section: Formation Of Carbon−oxygen Bondsmentioning

confidence: 99%

Gold-Catalyzed Carbon−Heteroatom Bond-Forming Reactions

2011

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“…The first microwave-assisted gold-catalyzed reaction was reported by Che in 2006 [23]. It is surprising that few papers have investigated microwave-assisted gold-catalyzed reactions [24][25][26]. Considering the many advantages of microwave-assisted reactions and its wide application in organic synthesis [27][28][29][30], it is attractive to apply microwave conditions to study gold-catalyzed annulation reactions.…”

Section: Introductionmentioning

confidence: 99%

A Rapid One-step Synthesis of Isoflavanone Compounds Under Microwave Irradiation

Dunn¹,

Do²,

Johnson³

et al. 2015

CMIC

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A rapid one-step synthesis of isoflavanones from salicylaldehydes and alkynes in the presence of gold(I) catalyst under microwave irradiation was developed. Various reaction conditions including catalysts, solvents, reaction time and temperature were investigated. This reaction is compatible with a variety of functional groups on salicylaldehydes or aromatic alkynes such as alkoxy, alkyl, halogen, amino, thiophenyl and pyridyl groups. NMR spectroscopy was used to monitor the reaction progress and to investigate the initial step in the mechanistic pathway.

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