Formal Total Synthesis of (+)-Lysergic Acid via Zinc(II)-Mediated Regioselective Ring-Opening Reduction of 2-Alkynyl-3-indolyloxirane

被引：61

作者：

Iwata, Akira ^{[1
]}

Inuki, Shinsuke ^{[1
]}

Oishi, Shinya ^{[1
]}

Fujii, Nobutaka ^{[1
]}

Ohno, Hiroaki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 13期

基金：

日本学术振兴会;

关键词：

(E)-BETA-ARYL VINYL HALIDES; ONE-POT SYNTHESIS; ASYMMETRIC EPOXIDATION; (+/-)-LYSERGIC ACID; ERGOT ALKALOIDS; EPOXIDES; CYCLIZATION; ALCOHOLS; EFFICIENT; OXIRANES;

D O I：

10.1021/jo2008324

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric formal synthesis of (+)-lysergic acid was achieved with a reductive ring-opening reaction of chiral 2-alkynyl-3-indolyloxirane with NaBH3CN as the key step. With Zn(OTf)(2) as an additive, the ring-opening reaction proceeded regioselectively at the 3-position to give the corresponding propargyl alcohol, which was a precursor of the allenic amide for palladium-catalyzed domino cyclization to construct the ergot alkaloid core structure.

引用

页码：5506 / 5512

页数：7

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