Synthesis and biological activity of diastereoisomeric octahydro-1H-indole-5,6,7-triols, analogues of castanospermine

A straightforward stereoselective route towards (3aR,5R,6S,7R,7aR)- and (3aR,5R,6S,7R,7aR)-octahydro-1H-indole-5,6,7-triol, analogues of castanospermine, starting from the corresponding shikimic acid derivatives is described. The key transformations of this approach are the Overman rearrangement and...

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Bibliographic Details
Published inTetrahedron Vol. 75; no. 3; pp. 398 - 408
Main Authors Gonda, Jozef, Široký, Michael, Martinková, Miroslava, Homolya, Samuel, Vilková, Mária, Pilátová, Martina Bago, Šesták, Sergej
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.01.2019
Elsevier
Subjects
[3,3]-Sigmatropic rearrangements
Antiproliferative activity
Chemistry
Chemistry, Organic
Glycosidase activity
Octahydro-1H-indoles
Physical Sciences
Ring-closing metathesis
Science & Technology
Transition states
Transition states
[3,3]-Sigmatropic rearrangements
Antiproliferative activity
Glycosidase activity
Ring-closing metathesis
Octahydro-1H-indoles
DISACCHARIDES
GLYCOSIDASE INHIBITORS
ANTICANCER ACTIVITY
GLUCOSIDASE
HOMOSPISULOSINE
DEOXYNOJIRIMYCIN
NATURAL OCCURRENCE
(+)-CASTANOSPERMINE
DERIVATIVES
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Summary:A straightforward stereoselective route towards (3aR,5R,6S,7R,7aR)- and (3aR,5R,6S,7R,7aR)-octahydro-1H-indole-5,6,7-triol, analogues of castanospermine, starting from the corresponding shikimic acid derivatives is described. The key transformations of this approach are the Overman rearrangement and ring-closing metathesis to form the diastereoisomeric cis-fused (5R,6S,7R)-octahydro-1H-indole-5,6,7-triols in good overall yields. Evaluation for in vitro cytotoxicity revealed for some prepared compounds significant antiproliferative activity and weak glycosidase inhibition. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.12.008