Synthesis of fused-ring cyclobutenones via a tandem [2 + 2] cycloaddition-.beta.-elimination sequence

Galatsis, Paul; Ashbourne, Katherine J.D.; Manwell, Jeffrey J.; Wendling, P.; Dufault, Robert; Hatt, Krista L.; Ferguson, George; Gallagher, John F.

doi:10.1021/jo00058a033

Cited by 7 publications

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“…We recently reported a general method for the construction of substituted cyclobutenone derivatives (1). To apply this methodology towards the construction of the natural product neofavelanone 1 (2), we required ready access to disubstituted indenone 2 (see Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Indenone synthesis. Improved synthetic protocol and effect of substitution on the intramolecular Friedel–Crafts acylation

Galatsis¹,

Manwell²,

Blackwell³

1994

Can. J. Chem.

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An improved protocol for the construction of substituted indenones is presented. Also the effect of substitution on the intramolecular Friedel–Crafts acylation was noted. Specifically, if there is no substitution at the 2-position of the indenone poor yields of cyclized material were obtained, if at all, while the substitution of a methyl or ethyl group greatly improved the yield of cyclized material. Placement of a large group (e.g., benzyl) resulted in a diminuation of the improved yield. The new synthetic procedure could, in principle, allow for the construction of 2,3-disubstituted indenones. One example of this reaction mode was presented.

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Section: Introductionmentioning

confidence: 99%

Indenone synthesis. Improved synthetic protocol and effect of substitution on the intramolecular Friedel–Crafts acylation

Galatsis¹,

Manwell²,

Blackwell³

1994

Can. J. Chem.

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ChemInform Abstract: Synthesis of Fused‐Ring Cyclobutenones via a Tandem (2 + 2) Cycloaddition ‐ β‐Elimination Sequence.

et al. 1993

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Synthesis of Fused-Ring Cyclobutenones via a Tandem (2 + 2) Cycloadditionβ-Elimination Sequence.-Photoreaction of the enol acetates (I) of 1,3-cyclohexanediones with the cycloalkenes (II) gives the fused cyclobutanes (III). These are converted into the corresponding cyclobutenes (IV) by base-induced . beta.-elimination of acetic acid. -(GALATSIS, P.; ASH-BOURNE, K. J.; MANWELL, J. J.; WENDLING, P.; DUFAULT, R.; HATT, K. L.; FERGUSON, G.; GALLAGHER, J. F.; J.

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Construction of fused bicyclic cyclooctane ring frameworks

Galatsis¹,

Manwell²

1995

Tetrahedron

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Synthesis of fused-ring cyclobutenones via a tandem [2 + 2] cycloaddition-.beta.-elimination sequence

Cited by 7 publications

References 0 publications

Indenone synthesis. Improved synthetic protocol and effect of substitution on the intramolecular Friedel–Crafts acylation

Indenone synthesis. Improved synthetic protocol and effect of substitution on the intramolecular Friedel–Crafts acylation

ChemInform Abstract: Synthesis of Fused‐Ring Cyclobutenones via a Tandem (2 + 2) Cycloaddition ‐ β‐Elimination Sequence.

Construction of fused bicyclic cyclooctane ring frameworks

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