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Volumn 61, Issue 16, 1996, Pages 5546-5556

Synthesis of novel glycosidase-inhibitory hydroxymethyl-substituted polyhydroxylated indolizidines: Ring-expanded analogs of the pyrrolizidine alkaloids alexine and australine

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE INHIBITOR; HOMOALEXINE; HOMOAUSTRALINE; INDOLIZIDINE DERIVATIVE; MANNOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0029785534     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960610a     Document Type: Article
Times cited : (84)

References (75)
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    • We initially investigated the use of an azido-chloro-alkene epoxidation precursor similar to that used in the quinolizidine work (see preceding paper in this journal). However, the Wittig olefination of lactol 15 proved problematic, leading primarily to elimination products.
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    • Note that the structure of 18E shown in Scheme 5 differs from the structure of 18E′ in Scheme 4 in two ways. First, the alkene π-face exposed to oxidant is different for each. Second, each lactone has a different ester π-face on the periphery of the ring. Structures with the same orientation of the ester but with different alkene π-faces exposed were higher in energy.
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    • The biological activity of 7-epialexine has not been reported. The screens performed by Nash et al. used potato amylose as the substrate, rather than p-nitrophenyl-α-glucopyranoside.
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