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. 2013 Aug 16;15(16):4070-3.
doi: 10.1021/ol401600j. Epub 2013 Aug 1.

Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes

Robert J Hinkle  1 , Shane E Lewis
Affiliations

Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes

Robert J Hinkle et al. Org Lett. .

Abstract

Reaction of 6-methyl-1-phenylhept-3-yne-2,6-diol with various aldehydes under Lewis acid conditions provides an atom economical, two-component cascade reaction sequence to novel 2,4-dihydro-1H-benzo[f]isochromene compounds. Aliphatic aldehydes as well as electron-deficient and -rich aromatic aldehydes can be used.

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Figures

Scheme 1
Scheme 1
Intermolecular Friedel-Crafts.
Scheme 2
Scheme 2
Retrosynthetic Analysis.
Scheme 3
Scheme 3
Air Oxidation of 3a and ORTEP of Lactone 4.
Scheme 4
Scheme 4
Mechanistic Rationale for Product Formation.
See this image and copyright information in PMC

References

    1. Sheldon RA. Chem Soc Rev. 2012;41:1437–1451. - PubMed
    2. Trost BM. Handbook of Green Chemistry. 2012;7:1–33.
    3. Trost BM. Angew Chem Int Ed, Engl. 1995;34:259–281.
    1. Touré BB, Hall DG. Chem Rev. 2009;109:4439–4486. - PubMed
    1. Kleinke AS, Webb D, Jamison TF. Tetrahedron. 2012;68:6999–7018.
    2. Nicolaou KC, Chen JS. Chem Soc Rev. 2009;38:2993–3009. - PMC - PubMed
    1. Tietze L-F. Domino Reactions in Organic Synthesis. Wiley-VCH; Weinheim: 2006. - PubMed

    1. For reactions described in the literature as cascade reactions, see: Horning BD, MacMillan DWC. J Am Chem Soc. 2013;135:6442–6445.Ohno H. Asian J Org Chem. 2013;2:18–28.Pintado-Sierra M, Rasero-Almansa AM, Corma A, Iglesias M, Sánchez F. J Cat. 2013;299:137–145.Surendra K, Qiu W, Corey EJ. J Am Chem Soc. 2011;133:9724–9726.Li H, Loh TP. Org Lett. 2010;12:2679–2681.Dalgard JE, Rychnovsky SD. Org Lett. 2005;7:1589–1591.

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