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Toward the Synthesis of SB-203207: Construction of Four Contiguous Nitrogen-Containing Stereogenic Centers
journal contribution
posted on 2019-11-19, 21:13 authored by Ichiro Hayakawa, Anna Nagayasu, Akira SakakuraSB-203207 is an altemicidin-type alkaloid that potently
inhibits
isoleucyl tRNA synthetase activity. Its main structural feature is
a hexahydro-6-azaindene framework containing a unique β-hydroxy
α,α-disubstituted α-amino acid moiety on the cyclopentane
portion. Herein we have established a method for constructing the
four contiguous nitrogen-containing stereogenic centers of SB-203207
by using as key steps the stereoselective alkylation of bowl-shaped
tricyclic lactone to construct a quaternary carbon at C1, the stereoselective
hydroboration–oxidation reaction to install the C2 hydroxy
group, and the Curtius rearrangement to introduce a nitrogen atom
onto the C1 quaternary carbon.
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quaternary carbonCurtius rearrangementstereoselective alkylationtricyclic lactoneContiguous Nitrogen-Containing Stereogenic Centers SB -203207hexahydro -6-azaindene frameworkC 2 hydroxy groupacid moietySB -203207nitrogen atomisoleucyl tRNA synthetase activityaltemicidin-type alkaloidcyclopentane portionC 1 quaternary carbonnitrogen-containing stereogenic centers
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