Total Synthesis of (+)-Gelsemine. Xuan Dong group seminar 12/19/2012
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1 Total Synthesis of (+)-Gelsemine Xuan Dong group seminar 12/19/2012
2 Historical Background of Gelsemine First detected the presence of alk aloids in extracts of G. sempervir ens in 1870 by Wormley. 1876, Sonnenschein isolated gels emine as the principal componen t of G. sempervirens The correct molecular formula o f gelsemine, C 20 H 22 N 2 O 2, was est ablished in 1910 by moore. Wormley, T. G. Am. J. Pharm. 1870, 42, 1-16; Sonnenschein, F. L. Ber. 1876, 9, ; Moorc, C. W. J. Chem. Soc. 1910, 97,
3 Gelsemine: A Synthetic Challenge Structure determinstion: Structure determined independently by the groups of Conroy and Wilson in 1959 via NMR and X-ray crystallography. Structural Challenge: Seven contiguous stereocenters [3.2.1] bicyclic system Spirooxindole system very little functionality Synthetic Interest: Racemic total syntheses: Speckamp, W. N. (1994) Johnson, A. P. (1994) Fukuyama, T. (1996) Hart, D. J. (1997) Overman (1999) Danishefsky (2002) Enantioselective total synthesis: Fukuyama (2000) Chakrabarti, J. K. Tetrahedron Lett.1959, 1 (4), 6 13; Lovell, F. M.; Pepinsky, R.; Wilson, A. J. C. Tetrahedron Lett. 1959, 1, 1 5; Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36 51
4 Speckamp and Hiemstra's Total Synthesis of (±)-Gelsemine 19 steps, 0.83% overall yield Speckamp et al, J. Chem. Soc., Chem. Commun. 1994, 767
5 Johnson s Total Synthesis of (±)-Gelsemine 29 steps, 0.58% overall yield Johnson, A. P. J. Chem. Soc., Chem. Commun. 1994, 763
6 Hart's Total Synthesis of (±)-Gelsemine 23 steps, 0.25% overall yield Hart, D. J et al. J. Am. Chem. Soc. 1997, 119, 6226
7 Overman's Total Synthesis of (±)-Gelsemine 26 steps, 1.2% overall yield Overman, L. E et al. Angew. Chem., Int. Ed. 1999, 38, 2934
8 Danishefsky s Total Synthesis of (±)-Gelsemine 36 steps, 0.02% overall yield Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 9812
9 Fukuyama's Total Synthesis of (±)-Gelsemine 32 steps, 0.67% overall yield T. Fukuyama, G. Liu, J. Am. Chem. Soc. 1996, 118,
10 Fukuyama's Enantioselective Total Synthesis of (+)-Gelsemine 31 steps, 0.86% overall yield Fukuyama, T et al. Angew. Chem., Int. Ed. 2000, 39, 4073
11 Why we synthesis Gelsemine? Bicyclo-[3.2.1] skeleton Spirooxindole structure Tetrahydropyran ring Pyrrolidine ring Yield Speckamp 1994 Intramolecular Mannich Intramolecular Heck Intramolecular oxymercuration 19 steps 0.83% Johnson 1994 Intramolecular Mannich Radical cyclization Intramolecular Mannich 29 steps 0.58% Fukuyama 1996 Hart 1997 Overman 1999 Danishefsky 2002 Fukuyama 2000 Cope rearrangement Radical cyclization Intramolecular Mannich Cope rearrangement Cope rearrangement Cope rearrangement Radical cyclization Intramolecular Heck [3,3]-Claisen rearrangement Cope rearrangement Intramolecular oxymercuration Intramolecular Hemiacetal formation Intramolecular lactone formation Intramolecular oxymercuration Intramolecular oxymercuration Intramolecular Mannich Oxetane ring opening Intramolecular Michael 32 steps 0.67% 23 steps 0.25% 26 steps 1.2% 36 steps 0.019% 31 steps 0.86% Key strategy in synthesis of Gelsemine
12 Organocatalysis: a new stream in organic synthesis Diels-Alder reaction 1,3-dipolarcycle addition Aldol condensation Manich reaction Michael addition Necleophilic Epoxidation Henry reaction ORGANOCATALYSIS Friedal-crafts additon Stercker reaction ɑ-oxygenation of carbonyl ɑ-amination of carbonyl ɑ-halogenation of carbonyl Pihko, P. M et al.. Chem. Rev. 2007, 107, List, B et al.. Chem. Rev. 2007, 107,
13 Synthesis of natural products by means of organo catalysis MacMillan.W. C et al. Nature, 2011, 475,
14 Retro-synthetic Analysis of (+)-Gelsemine
15 Synthesis the key structure of gelsemine by organocatalysis
16 Synthesis the Key Structure of (+)-Gelsemine
17 Synthesis D-ring and C-ring of (+)-gelsemine
18 Total Synthesis of (+)-Gelsemine
19
20 Total Synthesis of (+)-Gelsemine
21 Initial synthesis strategy Adjust synthesis strategy
22 Retro-synthetic Analysis of (+)-Gelsemine
23 Constuction the C5 and C16 stereocenter of gelsemine Hili, R.; Yudin, A. K. J. Am. Chem. Soc. 2006, 128, Fuji, K.; Kawabata, T.; Kriyu, Y.; Sugiura, Y. Heterocycles 1996, 42, 701
24 Region- and stereoselectivity addition of 116 to 115
25 Total Synthesis of (+)-Gelsemine
26 Construction the C-ring of gelsemine
27 Stereocontrolled synthesis C15 stereocenter
28 Stereocontrol synthesis C15 stereocenter
29 Total synthesis of (+)-gelsemine
30 Construction the D-ring of gelsemine
31 Construction the C6 stereocenter of gelsemine
32 Total synthesis of (+)-gelsemine
33 Total synthesis of (+)-gelsemine
34 Total synthesis of (+)-gelsemine via enol-oxonium cyclization
35 Stereocontrol synthesis C7 stereocenter
36 Total synthesis of (+)-gelsemine
37 Summary 25 steps with 1% overall yield. Angew. Chem. Int. Ed. 2012, 51,
38 Thank you! Happy holidays!
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