| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348051 | Tetrahedron: Asymmetry | 2006 | 8 Pages |
A carbohydrate based approach for the enantioselective synthesis of the polyketide acid unit present in nagahamide A has been reported. Reductive ring opening of a chiral cyclopropane ketone group to enantioselectively install the methyl and propyl groups, is a salient feature of this synthesis.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
3-O-Benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-d-xylo-oct-5E-enofuranos-7-uloseC18H22O5[α]D25=-63.7 (c 0.5, CHCl3)
3-O-Benzyl-5,6,8-trideoxy-1,2-O-isopropylidene-α-d-xylo-oct-5Z-enofuranos-7-uloseC18H22O5[α]D25=-37.2 (c 0.8, CHCl3)
3-O-Benzyl-5,6-C-methylene-5,6,8-trideoxy-1,2-O-isopropylidene-l-glycero-β-l-iodo-octos-7-ulofuranoseC19H24O5[α]D25=+7.2 (c 1.0, CHCl3)
5,6-C-Methylene-5,6,8-trideoxy-1,2-O-isopropylidene-l-glycero-β-l-iodo-octos-7-ulofuranoseC12H18O5[α]D25=+49.4 (c 1.0, CHCl3)
3,5-C-Dimethyl-3,5,6,7,8-pentadeoxy-1,2-O-isopropylidene-β-l-talo-octofuranoseC13H24O3[α]D25=+46.7 (c 1.0, CHCl3)
(4R,5S,6S)-2,2,5-Trimethyl-4-((S)-pentan-2-yl)-6-vinyl-1,3-dioxaneC14H26O2[α]D25=+25.6 (c 1.3, CHCl3)
(3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4,6-dimethyl-non-1-eneC18H38SiO2[α]D25=+3.9 (c 1.0, CHCl3)
(3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4,6-dimethyl-nonan-1-olC18H40SiO3[α]D25=-23.9 (c 0.8, CHCl3)
(7S,8S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-8,10-dimethyl-trideca-2,4-dienoic acid methyl esterC23H44SiO4[α]D25=-8.0 (c 0.7, CHCl3)
