New concise total synthesis of (+)-lentiginosine and some structural analogues

被引：80

作者：

Cardona, F

Moreno, G

Guarna, F

Vogel, P

Schuetz, C

Merino, P

Goti, A

机构：

[1] Univ Florence, CNR, ICCOM, Dipartimento Chim Organ Ugo Schiff, I-50019 Sesto Fiorentino, FI, Italy

[2] Ecole Polytech Fed Lausanne, Lab Glycochem & Asymmetr Synth LGSA, BCH, CH-105 Lausanne, Switzerland

[3] Univ Zaragoza, CSIC, Fac Ciencias ICMA, Dept Quim Organ,Lab Sintesis Asimetr, E-50009 Zaragoza, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 16期

关键词：

D O I：

10.1021/jo0509408

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.

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页码：6552 / 6555

页数：4

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