Regioselective route for arylnaphthalene lactones: convenient synthesis of taiwanin C, justicidin E, and daurinol
- Authors
- Park, Ju-Eun; Lee, Juyeun; Seo, Seung-Yong; Shin, Dongyun
- Issue Date
- 22-Jan-2014
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- Arylnaphthalene lactone; Intramolecular Diels-Alder; Regioselectivity; Lignan; Daurinol
- Citation
- TETRAHEDRON LETTERS, v.55, no.4, pp.818 - 820
- Journal Title
- TETRAHEDRON LETTERS
- Volume
- 55
- Number
- 4
- Start Page
- 818
- End Page
- 820
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/12891
- DOI
- 10.1016/j.tetlet.2013.12.014
- ISSN
- 0040-4039
- Abstract
- 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). (C) 2013 Elsevier Ltd. All rights reserved.
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