Total synthesis of (-)-martinellic acid via radical addition-cyclization-elimination reaction

被引：63

作者：

Shirai, Atsushi ^{[1
]}

Miyata, Okiko ^{[1
]}

Tohnai, Norimitsu ^{[2
]}

Miyata, Mikiji ^{[2
]}

Procter, David J. ^{[3
]}

Sucunza, David ^{[3
]}

Naito, Takeaki ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 6588558, Japan

[2] Osaka Univ, Grad Sch Engn, Suita, Osaka 5650871, Japan

[3] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 12期

关键词：

D O I：

10.1021/jo800560p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric total synthesis of martinellic acid, the first pyrrolo[3,2-c]quinoline alkaloid found in nature, is described. Three key steps in our synthesis of (-)-martinellic acid are the Bu3SnH-promoted radical addition-cyclization-elimination (RACE) reaction of an oxime ether with an alpha,beta-unsaturated ester to generate the pyrrolo[3,2-c]quinoline core, a chemoselective lactam carbonyl reduction, and guanidinylation under Mitsunobu reaction conditions. The key radical cyclization has also been investigated by using SmI2. (-)-Martinellic acid was synthesized from commercially available methyl 4-bromo-3-methylbenzoate in fewer steps than previous syntheses and in an improved overall yield.

引用

页码：4464 / 4475

页数：12

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