Difference between revisions of "File:Podophyllotoxin Syntheses.GIF"

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== Summary ==
 
== Summary ==
 
This picture shows two syntheses of (-)-Podophyllotoxin (structure 11). one starts from the top and the other from the bottom, and the two syntheses meet in the middle.  The first synthesis, J. AM. CHEM. SOC., Vol. 125, NO. 40, 2003, progresses from the top toward the center of the picture.  The starting material for the first synthesis is (4S)-2-(naphtho[2,3-d][1,3]dioxol-6-yl)-4-(propan-2-yl)-4,5-dihydro-1,3-oxazole (structure 16).  The second synthesis, Org. Lett., Vol. 9, No. 7, 2007, begins at the bottom of the picture and progresses toward the center.  The starting material for the second synthesis is 6-Bromo-1,3-Benzodioxole-5-Carbaldehyde (structure 1).
 
This picture shows two syntheses of (-)-Podophyllotoxin (structure 11). one starts from the top and the other from the bottom, and the two syntheses meet in the middle.  The first synthesis, J. AM. CHEM. SOC., Vol. 125, NO. 40, 2003, progresses from the top toward the center of the picture.  The starting material for the first synthesis is (4S)-2-(naphtho[2,3-d][1,3]dioxol-6-yl)-4-(propan-2-yl)-4,5-dihydro-1,3-oxazole (structure 16).  The second synthesis, Org. Lett., Vol. 9, No. 7, 2007, begins at the bottom of the picture and progresses toward the center.  The starting material for the second synthesis is 6-Bromo-1,3-Benzodioxole-5-Carbaldehyde (structure 1).
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== InChI ==
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'''Structure 1''' InChI=1/C8H5BrO3/c9-6-2-8-7(11-4-12-8)1-5(6)3-10/h1-3H,4H2
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'''Structure 2''' InChI=1/C10H9BrO4/c11-7-4-9-8(14-5-15-9)3-6(7)10-12-1-2-13-10/h3-4,10H,1-2,5H2
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'''Structure 3''' InChI=1/C17H20O6/c1-17(2,3)23-15(18)5-4-11-8-13-14(22-10-21-13)9-12(11)16-19-6-7-20-16/h4-5,8-9,16H,6-7,10H2,1-3H3/b5-4+
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'''Structure 4''' InChI=1/C29H36O9/c1-8-9-18(27(30)38-29(2,3)4)25(17-12-23(31-5)26(33-7)24(13-17)32-6)19-14-21-22(37-16-36-21)15-20(19)28-34-10-11-35-28/h8,12-15,18,25,28H,1,9-11,16H2,2-7H3/t18-,25-/m0/s1
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'''Structure 5''' InChI=1/C27H32O8/c1-8-9-18(26(29)35-27(2,3)4)24(16-10-22(30-5)25(32-7)23(11-16)31-6)19-13-21-20(33-15-34-21)12-17(19)14-28/h8,10-14,18,24H,1,9,15H2,2-7H3/t18-,24-/m0/s1
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'''Structure 6''' InChI=1/C26H30O9/c1-26(2,3)35-25(29)17(7-8-27)23(15-9-21(30-4)24(32-6)22(10-15)31-5)18-12-20-19(33-14-34-20)11-16(18)13-28/h8-13,17,23H,7,14H2,1-6H3/t17-,23-/m0/s1
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'''Structure 7''' InChI=1/C26H32O9/c1-26(2,3)35-25(29)22-16(11-27)23(28)15-10-18-17(33-12-34-18)9-14(15)21(22)13-7-19(30-4)24(32-6)20(8-13)31-5/h7-10,16,21-23,27-28H,11-12H2,1-6H3/t16-,21+,22-,23u/m0/s1
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'''Structure 8''' InChI=1/C26H30O9/c1-26(2,3)35-25(29)22-16(11-27)23(28)15-10-18-17(33-12-34-18)9-14(15)21(22)13-7-19(30-4)24(32-6)20(8-13)31-5/h7-10,16,21-22,27H,11-12H2,1-6H3/t16-,21+,22-/m0/s1
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'''Structure 9''' InChI=1/C23H24O9/c1-27-17-5-11(6-18(28-2)22(17)29-3)19-12-7-15-16(32-10-31-15)8-13(12)21(25)14(9-24)20(19)23(26)30-4/h5-8,14,19-20,24H,9-10H2,1-4H3/t14-,19+,20-/m0/s1
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'''Structure 10''' InChI=1/C23H26O9/c1-27-17-5-11(6-18(28-2)22(17)29-3)19-12-7-15-16(32-10-31-15)8-13(12)21(25)14(9-24)20(19)23(26)30-4/h5-8,14,19-21,24-25H,9-10H2,1-4H3/t14-,19+,20-,21-/m0/s1
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'''Structure 11''' InChI=1/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1
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'''Structure 12''' InChI=1/C22H20O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18-,19+/m1/s1
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'''Structure 13''' InChI=1/C33H34O9Si/c1-7-39-32(35)33-17-40-31(34)28(33)27(19-13-25(36-2)29(38-4)26(14-19)37-3)21-15-23-24(42-18-41-23)16-22(21)30(33)43(5,6)20-11-9-8-10-12-20/h7-16,27-28,30H,1,17-18H2,2-6H3/t27-,28+,30+,33+/m1/s1
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'''Structure 14''' InChI=1/C33H34O9SSi/c1-7-38-31(34)33(19-39-32(43)42-22-16-27(35-2)29(37-4)28(17-22)36-3)14-13-21-15-25-26(41-20-40-25)18-24(21)30(33)44(5,6)23-11-9-8-10-12-23/h7-18,30H,1,19-20H2,2-6H3/t30-,33+/m0/s1
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'''Structure 15''' InChI=1/C28H31NO5Si/c1-6-31-27(30)28(26-29-22(16-32-26)18(2)3)13-12-19-14-23-24(34-17-33-23)15-21(19)25(28)35(4,5)20-10-8-7-9-11-20/h6-15,18,22,25H,1,16-17H2,2-5H3/t22-,25+,28+/m1/s1
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'''Structure 16''' InChI=1/C17H17NO3/c1-10(2)14-8-19-17(18-14)12-4-3-11-6-15-16(21-9-20-15)7-13(11)5-12/h3-7,10,14H,8-9H2,1-2H3/t14-/m1/s1
  
 
== Licensing: ==
 
== Licensing: ==
 
{{PD-self}}
 
{{PD-self}}

Latest revision as of 13:04, 17 May 2010

Summary

This picture shows two syntheses of (-)-Podophyllotoxin (structure 11). one starts from the top and the other from the bottom, and the two syntheses meet in the middle. The first synthesis, J. AM. CHEM. SOC., Vol. 125, NO. 40, 2003, progresses from the top toward the center of the picture. The starting material for the first synthesis is (4S)-2-(naphtho[2,3-d][1,3]dioxol-6-yl)-4-(propan-2-yl)-4,5-dihydro-1,3-oxazole (structure 16). The second synthesis, Org. Lett., Vol. 9, No. 7, 2007, begins at the bottom of the picture and progresses toward the center. The starting material for the second synthesis is 6-Bromo-1,3-Benzodioxole-5-Carbaldehyde (structure 1).


InChI

Structure 1 InChI=1/C8H5BrO3/c9-6-2-8-7(11-4-12-8)1-5(6)3-10/h1-3H,4H2

Structure 2 InChI=1/C10H9BrO4/c11-7-4-9-8(14-5-15-9)3-6(7)10-12-1-2-13-10/h3-4,10H,1-2,5H2

Structure 3 InChI=1/C17H20O6/c1-17(2,3)23-15(18)5-4-11-8-13-14(22-10-21-13)9-12(11)16-19-6-7-20-16/h4-5,8-9,16H,6-7,10H2,1-3H3/b5-4+

Structure 4 InChI=1/C29H36O9/c1-8-9-18(27(30)38-29(2,3)4)25(17-12-23(31-5)26(33-7)24(13-17)32-6)19-14-21-22(37-16-36-21)15-20(19)28-34-10-11-35-28/h8,12-15,18,25,28H,1,9-11,16H2,2-7H3/t18-,25-/m0/s1

Structure 5 InChI=1/C27H32O8/c1-8-9-18(26(29)35-27(2,3)4)24(16-10-22(30-5)25(32-7)23(11-16)31-6)19-13-21-20(33-15-34-21)12-17(19)14-28/h8,10-14,18,24H,1,9,15H2,2-7H3/t18-,24-/m0/s1

Structure 6 InChI=1/C26H30O9/c1-26(2,3)35-25(29)17(7-8-27)23(15-9-21(30-4)24(32-6)22(10-15)31-5)18-12-20-19(33-14-34-20)11-16(18)13-28/h8-13,17,23H,7,14H2,1-6H3/t17-,23-/m0/s1

Structure 7 InChI=1/C26H32O9/c1-26(2,3)35-25(29)22-16(11-27)23(28)15-10-18-17(33-12-34-18)9-14(15)21(22)13-7-19(30-4)24(32-6)20(8-13)31-5/h7-10,16,21-23,27-28H,11-12H2,1-6H3/t16-,21+,22-,23u/m0/s1

Structure 8 InChI=1/C26H30O9/c1-26(2,3)35-25(29)22-16(11-27)23(28)15-10-18-17(33-12-34-18)9-14(15)21(22)13-7-19(30-4)24(32-6)20(8-13)31-5/h7-10,16,21-22,27H,11-12H2,1-6H3/t16-,21+,22-/m0/s1

Structure 9 InChI=1/C23H24O9/c1-27-17-5-11(6-18(28-2)22(17)29-3)19-12-7-15-16(32-10-31-15)8-13(12)21(25)14(9-24)20(19)23(26)30-4/h5-8,14,19-20,24H,9-10H2,1-4H3/t14-,19+,20-/m0/s1

Structure 10 InChI=1/C23H26O9/c1-27-17-5-11(6-18(28-2)22(17)29-3)19-12-7-15-16(32-10-31-15)8-13(12)21(25)14(9-24)20(19)23(26)30-4/h5-8,14,19-21,24-25H,9-10H2,1-4H3/t14-,19+,20-,21-/m0/s1

Structure 11 InChI=1/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

Structure 12 InChI=1/C22H20O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18-,19+/m1/s1

Structure 13 InChI=1/C33H34O9Si/c1-7-39-32(35)33-17-40-31(34)28(33)27(19-13-25(36-2)29(38-4)26(14-19)37-3)21-15-23-24(42-18-41-23)16-22(21)30(33)43(5,6)20-11-9-8-10-12-20/h7-16,27-28,30H,1,17-18H2,2-6H3/t27-,28+,30+,33+/m1/s1

Structure 14 InChI=1/C33H34O9SSi/c1-7-38-31(34)33(19-39-32(43)42-22-16-27(35-2)29(37-4)28(17-22)36-3)14-13-21-15-25-26(41-20-40-25)18-24(21)30(33)44(5,6)23-11-9-8-10-12-23/h7-18,30H,1,19-20H2,2-6H3/t30-,33+/m0/s1

Structure 15 InChI=1/C28H31NO5Si/c1-6-31-27(30)28(26-29-22(16-32-26)18(2)3)13-12-19-14-23-24(34-17-33-23)15-21(19)25(28)35(4,5)20-10-8-7-9-11-20/h6-15,18,22,25H,1,16-17H2,2-5H3/t22-,25+,28+/m1/s1

Structure 16 InChI=1/C17H17NO3/c1-10(2)14-8-19-17(18-14)12-4-3-11-6-15-16(21-9-20-15)7-13(11)5-12/h3-7,10,14H,8-9H2,1-2H3/t14-/m1/s1

Licensing:

Public domain I, the author of this work, hereby release it into the public domain. This applies worldwide.

In case this is not legally possible:
I grant anyone the right to use this work for any purpose, without any conditions, unless such conditions are required by law.

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current14:39, 14 May 2010Thumbnail for version as of 14:39, 14 May 2010814 × 1,287 (35 KB)Stefanet191 (talk | contribs)This picture shows two syntheses of (-)-Podophyllotoxin, one starts from the top and the other from the bottom, and the two syntheses meet in the middle. The first synthesis, J. AM. CHEM. SOC., Vol. 125, NO. 40, 2003, progresses from the top toward the c
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