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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.
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