Bioinspired Total Synthesis of Gymnothelignan N | Zendy

Huilin Li | Zendy; Yuanyuan Zhang | Zendy; Xingang Xie | Zendy; Haichen Ma | Zendy; Changgui Zhao | Zendy; Gaoyuan Zhao | Zendy; Xuegong She | Zendy

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Bioinspired Total Synthesis of Gymnothelignan N

Author(s) -

Huilin Li,

Yuanyuan Zhang,

Xingang Xie,

Haichen Ma,

Changgui Zhao,

Gaoyuan Zhao,

Xuegong She

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol501960j

Subject(s) - chemistry , total synthesis , intramolecular force , yield (engineering) , tetrahydrofuran , aldol reaction , phenol , dehydration , lignan , organic chemistry , catalysis , biochemistry , metallurgy , materials science , solvent

Bioinspired total synthesis of gymnothelignan N was accomplished in 13 steps and 6.7% overall yield. The synthesis features a syn Evans aldol reaction, an intramolecular hydrogenative dehydration reaction, and a phenol oxidative dearomatization/Friedel-Crafts reaction, which provides a new plausible biosynthetic pathway for the gymnothelignans and other symbiotic members. Meanwhile, another tetrahydrofuran-type lignan beilschmin A was also synthesized.

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