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Aminoglycoside antibiotics — Enantiomerically pure sporamine building blocks
Author(s) -
Seitz Bernhard,
Kühlmeyer Rainer,
Weller Thomas,
Meier Walter,
Ludin Christian,
Schwesinger Reinhard,
Knothe Lothar,
Prinzbach Horst
Publication year - 1989
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19891220922
Subject(s) - chemistry , diastereomer , azide , enantiomer , epoxide , aminoglycoside , stereochemistry , iodide , benzene , combinatorial chemistry , antibiotics , organic chemistry , catalysis , biochemistry
Starting from the 1,2:4,5‐dianhydro‐ epi ‐deoxyinositol 2a (available ultimately from benzene) and expedient total synthesis of rac ‐sporamine ( rac ‐ 3 ) has been developed. Key steps are two regiospecific and quantitative epoxide openings, effected intramolecularly in the diepoxyurethane 2b and intermolecularly by potassium iodide in the epoxyurethanes rac ‐ 4 , and the equally uniform substitution in the iodide rac ‐ 5d by hexa(tetra)methylguanidinium azide. The separation of diastereomeric esters with (−)‐camphanic acid ( 19 / 19 ′) opens the way to the pure enantiomers 3 / ent ‐ 3 . The scheme allows chemical modifications and provides sporamine equivalents in which only the OH group to be ultimately glycosidated remains unprotected.