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Total synthesis of (+/-)-trans-dihydronarciclasine through a highly endo-selective Diels-Alder cycloaddition of 3,5-dibromo-2-pyrone
- Authors
- Shin, In-Ji; Choi, Eun-Sil; Cho, Cheon-Gyu
- Issue Date
- Mar-2007
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- antitumor agents cycloaddition; lactones; natural products; total synthesis
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.46, no.13, pp.2303 - 2305
- Indexed
- SCIE
SCOPUS
- Journal Title
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Volume
- 46
- Number
- 13
- Start Page
- 2303
- End Page
- 2305
- ISSN
- 1433-7851
- Abstract
- Chemical Equation Presented) All essential functional groups in the natural product (±)-trans-dihydronarciclasine (1) were introduced with the correct relative configuration in a highly endo-selective Diels-Alder cycloaddition of 3,5-dibromo-2-pyrone with a styrene dienophile (see scheme). The total synthesis of 1 from these starting materials was completed in 11 steps and 15.8% overall yield.
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Related Researcher
- Cho, Cheon Gyu
- COLLEGE OF NATURAL SCIENCES (DEPARTMENT OF CHEMISTRY)