AN ASYMMETRIC TOTAL SYNTHESIS OF MARTINELLIC ACID

被引：4

作者：

Badarinarayana, Vivek ^{[1
]}

Mahmud, Hossen ^{[1
]}

Lovely, Carl J. ^{[1
]}

机构：

[1] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA

来源：

HETEROCYCLES | 2017年 / 95卷 / 02期

关键词：

Alkaloid; Pyrroloquinoline; Cross-Coupling Reaction; Cycloaddition Reaction; Guanidine; FORMAL TOTAL-SYNTHESIS; (-)-MARTINELLIC ACID; (+/-)-MARTINELLIC ACID; CYCLOADDITION APPROACH; CYCLIZATION REACTIONS; CORE; LACTONES; LACTAMS; AGENTS;

D O I：

10.3987/COM-16-S(S)81

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe an asymmetric total synthesis of the pyrrolo[3,2-c]quinoline natural product martinellic acid starting from pyrroglutamic acid. A convergent strategy involving a Pd-catalyzed aryl amination reaction of a chiral, non-racemic pyrrolidine derivative incorporates the C2-chiral center which controls the remaining two stereocenters. Elaboration of this adduct through a Grieco-elimination sets the stage for a diastereoselective intramolecular [3+2] azomethine ylide-alkene cycloaddition and the construction of the remaining two chiral centers. Elaboration of the cycloadduct and incorporation the prenyl guanidine units delivered martinellic acid after removal of the protecting groups.

引用

页码：1082 / 1105

页数：24

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