Towards a Total Synthesis of Anatoxin-a(s)
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1 Towards a Total Synthesis of Anatoxin-a(s) 2 P Me Me 2 Eric E. Buck Research Topic Seminar September 19, 2009 Eric Wipf Group Page 1 of 27 10/3/2009
2 Background Anatoxin-a(s) is a neurotoxin produced by the blue-green alga Anabaena flos-aquae (picture right) and A. lemmermannii A potent anticholinesterase with LD µg/ Kg in mice Inhibits AChE in the peripheral nervous system which leads to the build up of acetylcholine in the synaptic cleft Symptoms included muscle weakness, respiratory distress, and convulsions leading to death Responsible for the death of dogs, pigs, and ducks in the USA and Canada and water fowl in Denmark Aráoz, R., et al., Toxicon. 2009i, article in press. Matsunaga, S.; Moore, R. E.; iemezura, W. P. J. Am. Chem. Soc. 1989, 111, Eric Wipf Group Page 2 of 27 10/3/2009
3 Mechanism of Action 2 P Me Me 2 (AChE) 2 P Me Me 2 Anatoxin-a(s) Similar mechanism of action as Paraoxon, Physostigmine, Pyridostigmine, and the chemical weapon sarin. Et P Et 2 P F 2 Me 2 P Me Paraoxon Sarin Aráoz, R., et al., Toxicon. 2009i, article in press. Apeldoorn, M. E.; Egmond,. P.; Speijers, G. J. A.; Bakker, G. J. I. Mol. utr. Food Res. 2007, 51, Eric Wipf Group Page 3 of 27 10/3/2009
4 Biosynthesis Arginine Moore, B. S. at. Prod. Rep., 1999, 16, Moore, B. S.; htani, I.; de Koning, C. B.; Moore, R. E. Tetrahedron Lett. 1992, 33, Eric Wipf Group Page 4 of 27 10/3/2009
5 Biosynthesis Arginine Moore, B. S. at. Prod. Rep., 1999, 16, Moore, B. S.; htani, I.; de Koning, C. B.; Moore, R. E. Tetrahedron Lett. 1992, 33, Eric Wipf Group Page 5 of 27 10/3/2009
6 Biosynthesis Arginine Moore, B. S. at. Prod. Rep., 1999, 16, Moore, B. S.; htani, I.; de Koning, C. B.; Moore, R. E. Tetrahedron Lett. 1992, 33, Eric Wipf Group Page 6 of 27 10/3/2009
7 Biosynthesis Arginine Moore, B. S. at. Prod. Rep., 1999, 16, Moore, B. S.; htani, I.; de Koning, C. B.; Moore, R. E. Tetrahedron Lett. 1992, 33, Eric Wipf Group Page 7 of 27 10/3/2009
8 Biosynthesis 2 Anatoxin-a(s) 2 Me 2 P Me Me 2 2 Me 2 Moore, B. S. at. Prod. Rep., 1999, 16, Moore, B. S.; htani, I.; de Koning, C. B.; Moore, R. E. Tetrahedron Lett. 1992, 33, Eric Wipf Group Page 8 of 27 10/3/2009
9 Biosynthesis 2 Anatoxin-a(s) 2 Me 2 P Me Me 2 2 Me 2 Moore, B. S. at. Prod. Rep., 1999, 16, Moore, B. S.; htani, I.; de Koning, C. B.; Moore, R. E. Tetrahedron Lett. 1992, 33, Eric Wipf Group Page 9 of 27 10/3/2009
10 Biosynthesis 2 Anatoxin-a(s) 2 Me 2 P Me Me 2 2 Me 2 Moore, B. S. at. Prod. Rep., 1999, 16, Moore, B. S.; htani, I.; de Koning, C. B.; Moore, R. E. Tetrahedron Lett. 1992, 33, Eric Wipf Group Page 10 of 27 10/3/2009
11 Biosynthesis 2 Anatoxin-a(s) 2 Me 2 P Me Me 2 2 Me 2 Moore, B. S. at. Prod. Rep., 1999, 16, Moore, B. S.; htani, I.; de Koning, C. B.; Moore, R. E. Tetrahedron Lett. 1992, 33, Eric Wipf Group Page 11 of 27 10/3/2009
12 Biosynthesis 2 Anatoxin-a(s) 2 Me 2 P Me Me 2 2 Me 2 Moore, B. S. at. Prod. Rep., 1999, 16, Moore, B. S.; htani, I.; de Koning, C. B.; Moore, R. E. Tetrahedron Lett. 1992, 33, Eric Wipf Group Page 12 of 27 10/3/2009
13 Retro-synthesis TMS + R 2 R 1 2 P Me R 2 R 1 TMS Me 2 Anatoxin-a(s) Bz Eric Wipf Group Page 13 of 27 10/3/2009
14 Retro-synthesis TMS + R 2 R 1 2 P Me R 2 R 1 TMS Me 2 Anatoxin-a(s) Bz Eric Wipf Group Page 14 of 27 10/3/2009
15 Shi s work on the diamination of olefins R 1 R 3 + R 2 10 mol% Pd(PPh 3 ) 4 benzene-d 6 65 C R 3 R 2 R 1 substrate product substrate product Me (94%) Me Me (86%) Ph (90%) Me Ph Du,.; Zhao, B.; Shi, Y. J. Am. Chem. Soc., 2007, 129, Eric Wipf Group Page 15 of 27 10/3/2009
16 Shi s work on the diamination of olefins R 1 R 3 + R 2 10 mol% Pd(PPh 3 ) 4 benzene-d 6 65 C R 3 R 2 R 1 substrate product substrate product Me (94%) Me Me (86%) Ph (90%) Me Ph Du,.; Zhao, B.; Shi, Y. J. Am. Chem. Soc., 2007, 129, Eric Wipf Group Page 16 of 27 10/3/2009
17 Shi s work on the diamination of olefins R 2 R 1 R mol% Pd(PPh 3 ) 4 benzene-d 6 65 C R 3 R 2 R 1 substrate product substrate product product Me Me 2 C (94%) (60%) TMS Me Me 2 C Me TMS (90%) (86%) Ph (90%) Me Ph Du,.; Zhao, B.; Shi, Y. J. Am. Chem. Soc., 2007, 129, Eric Wipf Group Page 17 of 27 10/3/2009
18 Shi s work on the diamination of olefins + TFA 98% TFA C Et Et Et 98% Et 9.3 : 1 TFA, C, 96% 1) TFA, 80 C 2) Conc. Cl, reflux Ph 2 Ph 1 aq. a 2 Du,.; Zhao, B.; Shi, Y. J. Am. Chem. Soc., 2007, 129, Eric Wipf Group Page 18 of 27 10/3/2009
19 Shi s work on the diamination of olefins + TFA 98% TFA C Et Et Et 98% Et 9.3 : 1 TFA, C, 96% 1) TFA, 80 C 2) Conc. Cl, reflux Ph 2 Ph 1 aq. a 2 84% Du,.; Zhao, B.; Shi, Y. J. Am. Chem. Soc., 2007, 129, Eric Wipf Group Page 19 of 27 10/3/2009
20 Shi s work on the diamination of olefins R R R' Pd(0) R R R ' R Pd R R R Pd R ' R R Pd R ' Du,.; Zhao, B.; Shi, Y. J. Am. Chem. Soc., 2007, 129, Eric Wipf Group Page 20 of 27 10/3/2009
21 Route 1: diaminaiton of butadiene derivatives TMSCl, TEA DMF 48% TMS + Pd(PPh 3 ) 4 C 6 6, 65 C 3, - 78 C DCM, Me; Me 2 S TMS Eric Wipf Group Page 21 of 27 10/3/2009
22 Route 1: diaminaiton of butadiene derivatives TMSCl, TEA DMF 48% TMS + Pd(PPh 3 ) 4 C 6 6, 65 C 3, - 78 C DCM, Me; Me 2 S TMS Eric Wipf Group Page 22 of 27 10/3/2009
23 Route 1: diaminaiton of butadiene derivatives TMSCl, TEA DMF 48% TMS + Pd(PPh 3 ) 4 C 6 6, 65 C 3, - 78 C DCM, Me; Me 2 S TMS Eric Wipf Group Page 23 of 27 10/3/2009
24 Route 1: diaminaiton of butadiene derivatives TMSCl, TEA DMF 48% TMS + Pd(PPh 3 ) 4 C 6 6, 65 C 3, - 78 C DCM, Me; Me 2 S TMS Eric Wipf Group Page 24 of 27 10/3/2009
25 Route 1: diaminaiton of butadiene derivatives TESCl, LDA, MPA TF, -78 to 0 C 85% TES + Pd(PPh 3 ) 4 C 7 8 or TF, 65 C 40-67% TES Eric Wipf Group Page 25 of 27 10/3/2009
26 Route 1: diaminaiton of butadiene derivatives conditions or TES A B entry conditions yield , DCM, Me, -78 C; Me 2 S s 4, ai 4, TF, 2 mcpba, 5% ac 3 (aq), DCM; 1.5 M Cl, Me s 4, M, TF, 2 A: --- A: --- B: 5% a B: --- a Yield after isolation Eric Wipf Group Page 26 of 27 10/3/2009
27 Conclusion Route 1: diaminaiton of butadiene derivatives Route 2: ongoing Route 3: ongoing Screening conditions to close the ring asymmetrically Finish the synthesis Eric Wipf Group Page 27 of 27 10/3/2009
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