| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344414 | Tetrahedron: Asymmetry | 2011 | 6 Pages |
The stereoselective synthesis of (−)-synparvolide B, isolated from Syncolostemon parviflorus, has been accomplished from (S)-ethyl lactate. A 1,2-chelation controlled allylation, Sharpless asymmetric epoxidation, Brown asymmetric allylation and RCM reactions were used as the key steps.
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(2S,3S)-Hex-5-ene-2,3-diolC6H12O2[α]D25=+2.4 (c 1.6, CHCl3)Source of chirality: 1,2-chelation controlled allylationAbsolute configuration: (2S,3S)
(4S,5S)-4-Allyl-2,2,5-trimethyl-1,3-dioxolaneC9H16O2[α]D25=+0.4 (c 2.05, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S,5S)
(E)-Ethyl 4-((4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)but-2-enoateC12H20O4[α]D25=+2.2 (c 1.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (E,4S,5S)
(E)-4-((4S,5S)-2,2,5-Trimethyl-1,3-dioxolan-4-yl)but-2-en-1-olC10H18O3[α]D25=-4.7 (c 2.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (E,4S,5S)
((2S,3S)-3-(((4S,5S)-2,2,5-Trimethyl-1,3-dioxolan-4-yl)methyl)oxiran-2-yl)methanolC10H18O4[α]D25=-24.5 (c 1.65, CHCl3)Source of chirality: Sharpless asymmetric epoxidationAbsolute configuration: (2S,3S,4S,5S)
((S)-1-((4S,5S)-2,2,5-Trimethyl-1,3-dioxolan-4-yl)but-3-yn-2-olC10H16O3[α]D25=-7.8 (c 1.45, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,4S,5S)
(4S,5S)-4-((S)-2-(Methoxymethoxy)but-3-ynyl)-2,2,5-trimethyl-1,3-dioxolaneC12H20O4[α]D25=-106.0 (c 2.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S,5S,S)
(S)-4-(Methoxymethoxy)-5-((4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)pent-2-yn-1-olC13H22O5[α]D25=-19.1 (c 1.45, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,4S,5S)
(S,Z)-4-(Methoxymethoxy)-5-((4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)pent-2-en-1-olC13H24O5[α]D25=-84.6 (c 1.45, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,Z,4S,5S)
(4R,7S,Z)-7-(Methoxymethoxy)-8-((4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)octa-1,5-dien-4-olC16H28O5[α]D25=-21.8 (c 2.0, CHCl3)Source of chirality: Brown’s asymmetric allylationAbsolute configuration: (4R,7S,Z,4S,5S)
(4R,7S,Z)-7-(Methoxymethoxy)-8-((4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)octa-1,5-dien-4-yl acrylateC19H22O6[α]D25=-51.4 (c 1.7l, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,7S,Z,4S,5S)
(R)-6-((S,Z)-3-(Methoxymethoxy)-4-((4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)but-1-enyl)-5,6-dihydropyran-2-oneC17H26O6[α]D25=-26.75 (c 1.85, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S,Z,4S,5S)
(R)-6-((3S,5S,6S,Z)-5,6-Dihydroxy-3-(methoxymethoxy)hept-1-enyl)-5,6-dihydropyran-2-oneC14H22O6[α]D25=-16.5 (c 1.65, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,3S,5S,6S,Z)
(2S,3S,5S,Z)-5-(Methoxymethoxy)-7-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-6-ene-2,3-diyl diacetateC18H26O8[α]D25=-44.9 (c 0.95, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,5S,Z,R)
(2S,3S,5S,Z)-5-Hydroxy-7-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-6-ene-2,3-diyl diacetateC16H22O7[α]D25=-10.2 (c 2.35, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,5S,Z,R)
