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Asymmetric total synthesis of (+)-(3E)-pinnatifidenyne via abnormally regioselective Pd(0)-catalyzed endocyclization

Cited 3 time in Web of Science Cited 3 time in Scopus
Authors
Kim, Hyun Su; Kim, Taewoo; Ahn, Jungmin; Yun, Hwayoung; Lim, Changjin; Jang, Jaebong; Sim, Jaehoon; An, Hongchan; Surh, Young-Joon; Lee, Jeeyeon; Suh, Young-Ger
Issue Date
2018-02
Citation
Journal of Organic Chemistry, Vol.83 No.4, pp.1997-2005
Abstract
The asymmetric total synthesis of the marine natural product (+)-(3E)-pinnatifidenyne was accomplished. The key features of the synthesis involve the construction of an eight membered cyclic ether by the abnormally regioselective Pd(0)-catalyzed cyclization, the installation of a double bond in the oxocene skeleton by sequential in situ deconjugative isomerization, and the efficient introduction of the crucial chloride mediated by the substrate-controlled diastereoselective reduction.
ISSN
0022-3263
URI
https://hdl.handle.net/10371/172574
DOI
https://doi.org/10.1021/acs.joc.7b02937
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Graduate School of Convergence Science and Technology (융합과학기술대학원)Dept. of Molecular and Biopharmaceutical Sciences (분자의학 및 바이오제약학과)Journal Papers (저널논문_분자의학 및 바이오제약학과)
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