A Facile Synthesis of Isopongaflavone, Atalantoflavone Dimethylether, Racemoflavone Dimethyleter, and Methylenedioxy Isopongaflavone

Prasad, K. J. Rajendra; Periasamy, Prabu; Vijayalakshmi, C. S.

doi:10.1021/np50092a004

Cited by 7 publications

(1 citation statement)

References 11 publications

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“…121 In their efforts to develop an operationally simple, highly efficient reaction for the synthesis of diones 123-125, the authors envisaged that benz[b]indeno[2,1-e]pyran-10,11-dione 125 (isowrightiadione) could be obtained via the route highlighted by the retrosynthetic analysis in Scheme 28. It was expected that flavone 127 could be ob-tained by application of the Baker-Venkataraman rearrangement (129→128) followed by cyclization, 40,83,[122][123][124][125] whilst further cyclization would lead directly to the required compounds 125. 121 In the investigation of this route as a practical method to prepare this class of compound, the acylation of 2-hydroxyacetophenone (55) with mono-methyl phthalate (130), using a Steglich esterification procedure, gave 131 in 68% yield (Scheme 29).…”

Section: Syn Thesismentioning

confidence: 99%

Mechanism and Application of Baker–Venkataraman O→C Acyl Migration Reactions

Ameen

Snape

2014

Synthesis

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This literature review focuses on the O→C acyl migration of aryl esters to yield the corresponding 1,3-dicarbonyl products-a reaction known as the Baker-Venkataraman rearrangement-and outlines their subsequent transformations. The purpose of the review is to highlight the utility of the rearrangement which provides a key step in the synthesis of various heterocyclic motifs. The scope of the BakerVenkataraman rearrangement is illustrated by way of numerous examples of its application, and in doing so, the review contains over 100 references and covers just over 100 years of the literature, from the first report of the rearrangement by Auwers in 1910 up to more recent examples in the past few years.

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