| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348179 | Tetrahedron: Asymmetry | 2008 | 7 Pages |
The synthesis of all diastereomers of 4-benzyloxyhepta-1,6-diene-3,5-diols 8–10 is described. The diastereo- and enantioselectivity of palladium(II)-catalysed oxycarbonylation of the symmetric compounds 8–10 were studied. The substrates 8–10 underwent Pd(II)-initiated oxycarbonylative bicyclisation to afford bicyclic lactones 11–14 in good yields and with excellent threo-diastereoselectivity. Additionally, the synthesis of enantiomerically pure lactone d-gluco-12, precursor for syntheses of goniofufurone and 7-epi-goniofufurone, was developed.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(3R,5R)-4-Benzyloxyhepta-1,6-diene-3,5-diolC14H18O3[α]D20=+45 (c 0.50, CHCl3)Source of chirality: d-arabitol as starting materialAbsolute configuration: (3R,5R), (d-arabino)
(1R,5S,7R,8R)-8-Benzyloxy-7-vinyl-2,6-dioxabicyclo[3.3.0]octan-3-oneC15H16O4[α]D20=-29 (c 1.46, CHCl3)Source of chirality: d-arabitol as starting materialAbsolute configuration: (1R,5S,7R,8R), (d-gluco)
(1R,5S,7R,8S)-8-Benzyloxy-7-vinyl-2,6-dioxabicyclo[3.3.0]octan-3-oneC15H16O4[α]D20=-74 (c 0.15, CHCl3)Source of chirality: d-arabitol as starting materialAbsolute configuration: (1R,5S,7R,8S), (d-galacto)
