| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348579 | Tetrahedron: Asymmetry | 2007 | 10 Pages |
A key oxazolidinone synthon was obtained through condensation of vinyl magnesium with an epoxyimine, followed by a carbonation/cyclisation reaction in the presence of ammonium carbonate. Oxidative ozonolysis after protection and carbamolylation (optional) afforded the (5-O-carbamoyl-)polyoxamic derivatives in 9% (or 14%) total yield in six (or four) steps.
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(2S,3S,4R)-4-Benzylamino-4-tert-butyloxycarbonylamino-1-O-carbamoyl-2,3-dioxyisopropylidene-hex-5-enC22H32N2O6Ee = 89%[α]D25=-3.5 (c 1.26, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,4R)
(2S,3S,4S)-2-Benzyloxy-3-O,4-N-benzyl-carbamate-1-tert-butyldiphenylsilyloxy-pentanoïc acidC36H39NO6SiEe = 89%[α]D25=+22.4 (c 0.75, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,4R)
(4R,5S)-3-Benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-oneC22H24N2O5Ee = 89%[α]D25=+89.2 (c 1.70, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S,5S,1S)
(2S,3S,4S)-2-Benzyloxy-3-O,4-N-benzyl-carbamate-1-aminocarbonyloxypentanoïc acidC21H22N2O7Ee = 89%[α]D25=+8.6 (c 0.45, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,4S)
