Stereoselective synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-inositol systems via conduritols prepared from p-benzoquinone

被引：42

作者：

Podeschwa, M

Plettenburg, O

vom Brocke, J

Block, O

Adelt, S

Altenbach, HJ

机构：

[1] Berg Univ Wuppertal, Inst Organ Chem, D-42097 Wuppertal, Germany

[2] Berg Univ Wuppertal, Inst Biochem, D-42097 Wuppertal, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 10期

关键词：

natural products; asymmetric synthesis; chiral resolution; HPIC-IPAD;

D O I：

10.1002/ejoc.200200572

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis Of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity, ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

引用

页码：1958 / 1972

页数：15