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One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes.

Burroughs L, Eccleshare L, Ritchie J, Kulkarni O, Lygo B, Woodward S, Lewis W - Angew. Chem. Int. Ed. Engl. (2015)

Bottom Line: An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation.Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK).

No MeSH data available.


Variation of the 2-bromo(hetero)aryl aldehyde; yields starting from the commercial aldehydes are given.9 [a] The precursor aldehyde was obtained from isatin (3 steps).
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sch2: Variation of the 2-bromo(hetero)aryl aldehyde; yields starting from the commercial aldehydes are given.9 [a] The precursor aldehyde was obtained from isatin (3 steps).


One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes.

Burroughs L, Eccleshare L, Ritchie J, Kulkarni O, Lygo B, Woodward S, Lewis W - Angew. Chem. Int. Ed. Engl. (2015)

Variation of the 2-bromo(hetero)aryl aldehyde; yields starting from the commercial aldehydes are given.9 [a] The precursor aldehyde was obtained from isatin (3 steps).
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4581465&req=5

sch2: Variation of the 2-bromo(hetero)aryl aldehyde; yields starting from the commercial aldehydes are given.9 [a] The precursor aldehyde was obtained from isatin (3 steps).
Bottom Line: An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation.Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK).

No MeSH data available.