Bioinspired Total Synthesis of Gymnothelignan N

被引：24

作者：

Li, Huilin ^{[1
]}

Zhang, Yuanyuan ^{[1
]}

Xie, Xingang ^{[1
]}

Ma, Haichen ^{[1
]}

Zhao, Changgui ^{[1
]}

Zhao, Gaoyuan ^{[1
]}

She, Xuegong ^{[1
,2
]}

机构：

[1] Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 17期

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; COUPLING REACTION; CONSTRUCTION; TETRAHYDROFURAN; EUPOMATILONE-6; CORE; LIGNANS; SYSTEM; ETHER; ACID;

D O I：

10.1021/ol501960j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4440 / 4443

页数：4

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