| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348758 | Tetrahedron: Asymmetry | 2006 | 4 Pages |
A new and convergent synthetic route for (5RS)-Hagen’s lactones 1–4 is described, starting from bisacetonide mannofuranolactone 5. The key transformations in the synthesis are SmI2 mediated α-deoxygenation of a aldonolactone to 2-deoxy lactone, Pd(II) mediated oxidative cyclization and an oxidation of tetrahydrofuran to a furanone.
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2,2-Dimethyl-6-vinyl-dihydrofuro-[3,4-d][1,3]dioxal-4-oneC9H12O4[α]D21=+31.9 (c 0.8, CHCl3)Source of chirality: d-mannose
4-Hydroxy-5-vinyl-dihydro-furan-2-oneC6H8O3[α]D21=+21.5 (c 1.0, CHCl3)Source of chirality: d-mannose
Hex-5-ene-1,3,4-triolC6H12O3[α]D21=+9.1 (c 0.5, D2O)Source of chirality: d-mannose
2-Vinyl-tetrahydro-furan-3-olC6H10O2[α]D21=+26.1 (c 0.85, CHCl3)Source of chirality: d-mannose
