Intramolecular Dehydro-Diels–Alder Reaction Affords Selective Entry to Arylnaphthalene or Aryldihydronaphthalene Lignans | Zendy

Laura S. Kocsis | Zendy; Kay M. Brummond | Zendy

Open Access

Intramolecular Dehydro-Diels–Alder Reaction Affords Selective Entry to Arylnaphthalene or Aryldihydronaphthalene Lignans

Author(s) -

Laura S. Kocsis,

Kay M. Brummond

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol501853y

Subject(s) - intramolecular force , chemistry , diels–alder reaction , lignan , organic chemistry , catalysis

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.

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