| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346004 | Tetrahedron: Asymmetry | 2012 | 12 Pages |
The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamaguchi macrolactonization, and ring-closing metathesis.
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(1S,3R)-1′-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)butane-1,3-diolC9H18O4[α]D25=-4.2 (c 1.0, CHCl3)Source of chirality: d-mannitol, stereoselective synthesisAbsolute configuration: (1′R,1S,3R)
(1S,3S)-1′-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)butane-1,3-diolC9H18O4[α]D25=+22.5 (c 0.33, CHCl3)Source of chirality: d-mannitol, stereoselective synthesisAbsolute configuration: (1′R,1S,3S)
(5S,7R)-5′-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2,7,10,10-pentamethyl-3,3,9,9-tetraphenyl-4,8-dioxa-3,9-disilaundecaneC41H54O4Si2[α]D25=+13.2 (c 2.0, CHCl3)Source of chirality: d-mannitol, stereoselective synthesisAbsolute configuration: (5′R,5S,7R)
(2R,3S,5R)-3,5-Bis(tert-Butyldiphenylsilyloxy)hexane-1,2-diolC38H50O4Si2[α]D25=-3.1 (c 1.05, CHCl3)Source of chirality: d-mannitol, stereoselective synthesisAbsolute configuration: (2R,3S,5R)
(5R,7S)-2,2,5,10,10-Pentamethyl-3,3,9,9-tetraphenyl-7-vinyl-4,8-dioxa-3,9-disilaundecaneC38H48O2Si2[α]D25=+12.8 (c 0.8, CHCl3)Source of chirality: d-mannitol, stereoselective synthesisAbsolute configuration: (5R,7S)
(2R,4S)-Hex-5-ene-2,4-diolC6H12O2[α]D25=-3.2 (c 0.45, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (2R,4S)
(R)-1-(4-Benzyl-2-thioxothiazolidin-3-yl)ethanoneC12H13NOS2[α]D25=-210.0 (c 1.0, CHCl3)Source of chirality: d-phenylalanine, asymmetric synthesisAbsolute configuration: (4R)
(S)-1-((R)-4-Benzyl-2-thioxothiazolidin-3-yl)-3-hydroxypent-4-en-1-oneC15H17NO2S2[α]D25=-166.4 (c 0.8, CHCl3)Source of chirality: d-phenylalanine, asymmetric synthesisAbsolute configuration: (4R,8S)
(R)-1-((R)-4-Benzyl-2-thioxothiazolidin-3-yl)-3-hydroxypent-4-en-1-oneC15H17NO2S2[α]D25=-114.5 (c 0.9, CHCl3)Source of chirality: d-phenylalanine, asymmetric synthesisAbsolute configuration: (4R,8R)
(S)-3-Hydroxy-N-methoxy-N-methylpent-4-enamideC7H13NO3[α]D25=-28.9 (c 0.55, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S)
(S)-4-Hydroxyhex-5-en-2-oneC6H10O2[α]D25=-180.0 (c 0.15, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S)
(2R,4S)-4-(tert-Butyldiphenylsilyloxy)hex-5-en-2-olC22H30O2Si[α]D25=-5.3 (c 1.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4S)
(3S,5R)-5-(tert-Butyldiphenylsilyloxy)hex-1-en-3-olC22H30O2Si[α]D25=+5.0 (c 1.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,5R)
(S)-6-(Benzyloxy)hex-1-en-3-olC13H18O2[α]D25=+2.5 (c 1.0 , CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (6S)
(S)-(6-(Benzyloxy)hex-1-en-3-yloxy)(tert-butyl)diphenylsilaneC29H36O2Si[α]D25=+16.5 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (6S)
(S)-4-(tert-Butyldiphenylsilyloxy)hex-5-en-1-olC22H30O2Si[α]D25=+17.5 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S)
(S)-4-(tert-Butyldiphenylsilyloxy)hex-5-enoic acidC22H28O3Si[α]D25=+14.5 (c 0.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S)
(S)-((2R,4S)-4′-(tert-Butyldiphenylsilyloxy)hex-5-en-2-yl) 4-(tert-butyldiphenylsilyloxy)hex-5-enoateC44H56O4Si2[α]D25=-48.3 (c 0.33, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4S,4′S)
(S)-((2R,4S)-4′-Hydroxyhex-5-en-2-yl) 4-hydroxyhex-5-enoateC12H20O4[α]D25=-28.8 (c 0.5, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4S,4′S)
(4S,6R)-4′-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2,6-trimethyl-1,3-dioxaneC12H22O4[α]D25=-37.6 (c 1.0, CHCl3)Source of chirality: d-mannitol, asymmetric synthesisAbsolute configuration: (4S,4′R,6R)
(4S,6S)-4′-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2,6-trimethyl-1,3-dioxaneC12H22O4[α]D25=+3.4 (c 3.1, CHCl3)Source of chirality: d-mannitol, asymmetric synthesisAbsolute configuration: (4S,4′R,6S)
(5S,8S,10R,E)-5,8-Dihydroxy-10-methyl-3,4,5,8,9,10-hexahydro-2H-oxecin-2-oneC10H16O4[α]D25=+43.9 (c 1.0, MeOH);Source of chirality: asymmetric synthesisAbsolute configuration: (5S,8S,10R,E)
