Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamines

被引：15

作者：

Anton-Torrecillas, Cintia

Gonzalez-Gomez, Jose C. ^{[1
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 36期

关键词：

TERT-BUTANESULFINAMIDE; TYLOPHORA-ASTHMATICA; ALKALOIDS; (S)-(+)-TYLOPHORINE; CARBOAMINATION; TETRAPONERINES; PROLINE;

D O I：

10.1039/c4ob01133c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient stereocontrolled preparation of chiral phenanthroindolizidines is detailed. The synthesis relies on the stereoselective indium-mediated allylation of 2-(phenanthren-9-yl) acetaldehyde derivatives with chiral tert-butylsulfinamide. Chemoselective transformations from the corresponding homoallylic sulfinamine allow the synthesis of the phenanthroindolizidines in only three synthetic operations, without any detectable racemization. Following this procedure, the synthesis of natural (-)-tylophorine was successfully accomplished.

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页码：7018 / 7025

页数：8

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