Asymmetric syntheses of 2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-D-glucitol [(+)-ADGDP]

被引：17

作者：

Davies, Stephen G. ^{[1
]}

Figuccia, Aude L. A. ^{[1
]}

Fletcher, Ai M. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

来源：

TETRAHEDRON | 2014年 / 70卷 / 22期

关键词：

(+)-DGDP; (+)-ADGDP; Pyrrolidine alkaloids; Asymmetric synthesis; RING-CLOSING IODOAMINATION; AMIDE CONJUGATE ADDITION; POLYHYDROXYLATED PYRROLIDINES; D-FRUCTOSE; INTRAMOLECULAR CYCLIZATION; ABSOLUTE-CONFIGURATION; (-)-MARTINELLIC ACID; UNSATURATED AMINES; INHIBITORS; DERIVATIVES;

D O I：

10.1016/j.tet.2014.03.100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric syntheses of 2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-D-glucitol [(+)-ADGDP] were achieved via the ring-closing iodoamination of an enantiopure bishomoallylic amine, followed by functionalisation of the resultant iodomethyl substituted pyrrolidine. In the case of (+)-DGDP, formation of the corresponding aziridinium ion followed by regioselective ring-opening with H2O gave the desired hydroxymethyl substituted pyrrolidine as a single diastereoisomer (>99:1 dr), with subsequent deprotection giving (+)-DGDP in good yield. Whereas in the case of (+)-ADGDP, displacement of iodide with NaN3 proved to be optimal, giving (+)-ADGDP in good yield after reduction and deprotection. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3601 / 3607

页数：7

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