Synthesis and sequential diastereoselective incorporation of hydroxyl groups into hexahydrofuro[3,2-]indolizin-7(2)-one to give mono-, di- and tetra-hydroxyfuroindolizidines

Dihydrofuro[2,3- f ]indolizidinone obtained from biosourced reagents even at multigram-scale was used as an advanced building-block with up to five points of chemical diversification. This resulted in the sequential synthesis of a series of mono-, di- and tetra-hydroxyfuranoindolizidines belonging t...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-08, Vol.18 (32), p.6384-6393
Main Authors: Šafá, Peter, Marchalín, Štefan, Cve ko, Matej, Moncol, Ján, Dujni, Viera, Šoral, Michal, Daïch, Adam
Format: Article
Language:English
Subjects:
Acetic acid
Amides
Carbonyl compounds
Carbonyls
Crystallography
Diols
Epoxidation
Hydroxyl groups
NMR
Nuclear magnetic resonance
Reagents
Ring opening
Sequences
Stereoselectivity
Tetrahydrofuran
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Summary:Dihydrofuro[2,3- f ]indolizidinone obtained from biosourced reagents even at multigram-scale was used as an advanced building-block with up to five points of chemical diversification. This resulted in the sequential synthesis of a series of mono-, di- and tetra-hydroxyfuranoindolizidines belonging to a very scarce and elaborate tetrahydrofuran-fused indolizidine family with up to six controlled stereogenic centers. These sequences include, among others, diastereoselective olefin epoxidation, stereoselective epoxide ring opening into tetrahydrofuran trans -diols, their protection as an ester or acetonide, and lactam carbonyl reduction ultimately followed by acetate or acetonide deprotection. Sequential synthesis of a series of furan-fused bicyclic iminosugar derivatives such as mono-, di- and tetrahydroxyfurano-indolizidines has been developed.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00896f