Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 13, Pages 1704-1712Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601611
Keywords
Total synthesis; Natural products; Annulation; Cross-coupling; Lactones
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Funding
- Korea Institute of Science and Technology (KIST) institutional program [2Z04930]
- Ministry of Trade, Industry & Energy (MOTIE, Korea) [N0000885]
- Korea Evaluation Institute of Industrial Technology (KEIT) [N0000885] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
- Ministry of Science & ICT (MSIT), Republic of Korea [2Z04970] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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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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