Asymmetrized tris(hydroxymethyl)methane as a precursor of N- and O-containing 6-membered heterocycles through ring-closing metathesis

被引：20
作者：
Banfi, L [1 ]
Guanti, G [1 ]
Paravidino, M [1 ]
Riva, R [1 ]
机构：
[1] Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 09期
关键词：
D O I：
10.1039/b502952j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel synthetic application of asymmetrized tris(hydroxymethyl)rnethane (THYM*) 1, obtained in both enantiomeric forms in high e.e. via a chemoenzymatic procedure, is described. Starting from the common precursor 3, N- and O-containing 6-membered heterocycles have been prepared exploiting ring-closing metathesis as the key step. Possible elaborations of the double bond in 6 and 28 have been explored and, in the case of 28, conversion into the glycosidase inhibitor isofagomine 53 has been achieved.
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收藏
页码：1729 / 1737
页数：9
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