2-hydroxycastanospermines (dihydroxy-L-swainsonines) from octonolactones: Inhibition of naringinase (L-rhamnosidase)

被引：37

作者：

Bell, AA

Pickering, L

Watson, AA

Nash, RJ

Griffiths, RC

Jones, MG

Fleet, GWJ

机构：

[1] DYSON PERRINS LAB,OXFORD CTR MOL SCI,OXFORD OX1 3QY,ENGLAND

[2] INST GRASSLAND & ENVIRONM RES,ABERYSTWYTH SY23 3EB,CARDIGANSHIRE,WALES

[3] UNIV WALES,INST BIOL SCI,ABERYSTWYTH SY23 3DD,CARDIGANSHIRE,WALES

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 47期

关键词：

D O I：

10.1016/0040-4039(96)01956-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Short syntheses of 2S-2-hydroxycastanospermine, and 2R- and 2S-2-hydroxy-6-epicastanospermine - in which there are 6 adjacent chiral centres and 8 contiguous carbon atoms containing functional groups from eight carbon sugar lactones - depend on efficient cyclisations to give piperidines with trans-acetonides as protecting groups. Inhibition of naringinase (L-rhamnosidase) by 2S-2-hydroxy-6-epicastanospermine and 2S-2-hydroxycastanospermine may be due to a structural resemblance to the unnatural L-(+)-swainsonine. Copyright (C) 1996 Elsevier Science Ltd

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页码：8561 / 8564

页数：4

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