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Org Lett. 2014 Aug 15;16(16):4158-61. doi: 10.1021/ol501853y. Epub 2014 Jul 25.

Intramolecular dehydro-Diels-Alder reaction affords selective entry to arylnaphthalene or aryldihydronaphthalene lignans.

Author information

1
Department of Chemistry, University of Pittsburgh , 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, United States.

Abstract

Intramolecular dehydro-Diels-Alder (DDA) reactions are performed affording arylnaphthalene or aryldihydronaphthalene lactones selectively as determined by choice of reaction solvent. This constitutes the first report of an entirely selective formation of arylnaphthalene lactones utilizing DDA reactions of styrene-ynes. The synthetic utility of the DDA reaction is demonstrated by the synthesis of taiwanin C, retrohelioxanthin, justicidin B, isojusticidin B, and their dihydronaphthalene derivatives. Computational methods for chemical shift assignment are presented that allow for regioisomeric lignans to be distinguished.

PMID:
25061845
PMCID:
PMC4136723
DOI:
10.1021/ol501853y
[Indexed for MEDLINE]
Free PMC Article

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