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An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides
- Issue Date
- 3-Apr-2017
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Total synthesis; Natural products; Annulation; Cross-coupling; Lactones
- Citation
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no.13, pp.1704 - 1712
- Journal Title
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Number
- 13
- Start Page
- 1704
- End Page
- 1712
- ISSN
- 1434-193X
- Abstract
- A simple method for the preparation of arylnaphthalene lactone natural products was developed and used to synthesize diphyllin (10), justicidin A (12), cilinaphthalide B (13), taiwanin E (15), chinensinaphthol (16), taiwanin E methyl ether (17), chinensinaphthol methyl ether (18), justicidin C (21), and justicidin D (22). Key steps of the syntheses include the Hauser-Kraus annulation of cyanophthalides 7a and 7b and Suzuki-Miyaura cross-coupling reactions between arylnaphthalene lactones that contain a sulfonate group (i.e., 9, 14, 19, and 20) and various potassium aryltrifluoroborates.
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Related Researcher
- Kang, Ki Sung
- College of Korean Medicine (Premedical course of Oriental Medicine)