Regioselective route for arylnaphthalene lactones: convenient synthesis of taiwanin C, justicidin E, and daurinol

•Type I and Type II of arylnaphthalene lactones were synthesized regioselectively.•Arylalkene–arylalkynes were used in the intramolecular Diels–Alder reaction.•Dihydronaphthalene lactones were converted to arylnaphthalene lactones by DDQ.•We report the synthesis of Type I taiwanin C, daurinol, and T...

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Bibliographic Details
Published in:Tetrahedron letters 2014-01, Vol.55 (4), p.818-820
Main Authors: Park, Ju-Eun, Lee, Juyeun, Seo, Seung-Yong, Shin, Dongyun
Format: Article
Language:English
Subjects:
Antiinfectives and antibacterials
Arylnaphthalene lactone
Blocking
Daurinol
Diels-Alder reactions
Diuretics
Intramolecular Diels–Alder
Ion channels
Lactones
Lignan
Regioselectivity
Synthesis (chemistry)
Tetrahedrons
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Summary:•Type I and Type II of arylnaphthalene lactones were synthesized regioselectively.•Arylalkene–arylalkynes were used in the intramolecular Diels–Alder reaction.•Dihydronaphthalene lactones were converted to arylnaphthalene lactones by DDQ.•We report the synthesis of Type I taiwanin C, daurinol, and Type II justidicin E. Arylnaphthalene lactones are natural products which can be isolated from a wide range of plants and have the significant biological activities including cytotoxicity, antimicrobial, diuretic, and ion channel blocking. The drawback of the previous intramolecular Diels–Alder reaction of 3-arylprop-2-ynyl 3-arylpropiolates was to generate two regioisomers of arylnaphthalene lactone without selectivity. Herein, we report a convenient and regioselective synthesis method in which the intramolecular Diels–Alder reaction of an arylalkene–arylalkyne and subsequent DDQ oxidation was used for Type I and Type II arylnaphthalene lactones, respectively. We demonstrated the synthesis of three lignans, taiwanin C (Type I), justicidin E (Type II), and daurinol (Type I and anti-cancer activity).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.12.014