Asymmetric formal synthesis of (+)-cycloclavine

被引：12

作者：

Chen, Jin-Quan ^{[1
]}

Song, Le-Le ^{[1
]}

Li, Feng-Xing ^{[1
]}

Shi, Zi-Fa ^{[1
]}

Cao, Xiao-Ping ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 96期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; VINYLOGOUS MANNICH REACTIONS; TERT-BUTANESULFINYL IMINES; ERGOT ALKALOIDS; SELECTIVE SYNTHESIS; CLAVINE ALKALOIDS; ALLENYL ALCOHOLS; (+/-)-CYCLOCLAVINE; LACTONES; AMINES;

D O I：

10.1039/c7cc08044a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric synthesis of Szantay's amine (+)-2, the pivotal precursor for direct access to (+)-cycloclavine (1), is described for the first time in eleven steps with 19.7% overall yield from the commercially available 4-bromoindole. The strategy features an asymmetric induction by Ellman's sulfinimine and rhodium-catalysed isomerization of the C=C bond.

引用

页码：12902 / 12905

页数：4

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