| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344366 | Tetrahedron: Asymmetry | 2011 | 7 Pages |
The total syntheses of the first examples of diarylheptanoid natural products (5S)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone 1, and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane 2 isolated from the rhizomes of Zingiber officinale were accomplished using Sharpless epoxidation and cross-metathesis reactions as the key steps.
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(2S,3S)-3-[4-(Benzyloxy)-3-methoxyphenethyl]oxiran-2-ylmethanolC19H22O4[α]D25=-23.0 (c 1.0, CHCl3)Source of chirality: Sharpless asymmetric epoxidationAbsolute configuration: (2S,3S)
(3S)-5-[4-(Benzyloxy)-3-methoxyphenyl]pentane-1,3-diolC19H24O4[α]D25=-9.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S)
(4S)-4-[4-(Benzyloxy)-3-methoxyphenethyl]-2-(4-methoxyphenyl)-1,3-dioxane-olC27H30O5[α]D25=-38.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S)
(3S)-5-[4-(Benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-olC27H32O5[α]D25=+14.6 (c 0.75, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S)
(5S)-7-[4-(Benzyloxy)-3-methoxyphenyl]-5-[(4-methoxybenzyl)oxy]-1-hepten-3-oneC29H32O5[α]D25=+8.6 (c 0.75, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (5S)
(E,5S)-1,7-Di[4-(benzyloxy)-3-methoxyphenyl]-5-[(4-methoxybenzyl)oxy]-1-hepten-3-oneC43H44O[α]D25=+5.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (E,5S)
(E,5S)-1,7-Di[4-(benzyloxy)-3-methoxyphenyl]-5-hydroxy-1-hepten-3-oneC35H36O6[α]D25=+78.0 (c 0.25, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (E,5S)
(1S,4E)-1-[4-(Benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetateC37H38O7[α]D25=+7.2 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,4E)
(5S)-5-Acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanoneC23H28O7[α]D25=+5.0 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (5S)
(1S,3R,4E)-1-[4-(Benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-hydroxy-4-pentenyl acetateC37H40O7[α]D25=+4.5 (c 1.0, CHCl3)Source of chirality: CBS reductionAbsolute configuration: (1S,3R,4E)
(1S,3R,4E)-3-(Acetyloxy)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-4-pentenyl acetateC39H42O8[α]D25=-14.5 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,3R,4E)
(3S,5S)-3,5-Diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptaneC25H32O8[α]D25=+8.5 (c 1.25, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,5S)
