3 years ago

Asymmetric Total Synthesis of (+)-(3E)-Pinnatifidenyne via Abnormally Regioselective Pd(0)-Catalyzed Endocyclization

Asymmetric Total Synthesis
of (+)-(3E)-Pinnatifidenyne via Abnormally
Regioselective Pd(0)-Catalyzed
Endocyclization
Hongchan An, Jaehoon Sim, Hwayoung Yun, Taewoo Kim, Jeeyeon Lee, Changjin Lim, Jungmin Ahn, Jaebong Jang, Hyun Su Kim, Young-Ger Suh, Young-Joon Surh
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02937

DOI: 10.1021/acs.joc.7b02937

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