کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1348179 | 980343 | 2008 | 7 صفحه PDF | دانلود رایگان |
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.
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(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)
Journal: Tetrahedron: Asymmetry - Volume 19, Issue 1, 30 January 2008, Pages 38–44