The Story of Hyperforin Exploring Path to Concise Synthesis
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1 Exploring Path to Concise Synthesis Presenter: Advisor: Prof. Dong The University of Texas at Austin If a man keeps cherishing his old knowledge, so as continually to be acquiring new, he may be a teacher of others Confucius1
2 Part 1. A Brief Introduction of PPAPs PPAPs: Polycyclic Polyprenylated Acylphloroglucinols Isolation: mainly from Hypericum perforatum ( 贯叶连翘 ) and other plants from the family Guttiferae ( 金丝桃科 ) and related families; over 150 natural products Structural features: bicyclo[3.3.1]nonane or bicyclo[3.2.1]octane Hypericum perforatum (St. John s wort) Ciochina, R.; Grossman, R. B. Chem. Rev. 2006, 106,
3 3 Classes of PPAPs Part 1. A Brief Introduction of PPAPs Biosynthesis of PPAPs Stage 1: Biosynthesis of MPAPs from CoAs Ciochina, R.; Grossman, R. B. Chem. Rev. 2006, 106,
4 Part 1. A Brief Introduction of PPAPs Stage 2: Biosynthesis of PPAPs from MPAPs (R 2 = prenyl) Ciochina, R.; Grossman, R. B. Chem. Rev. 2006, 106,
5 Part 2. Synthetic Strategies towards bicyclo[3.3.1]nonane Stoltz s Preliminary Work (2002): Effenberger Cyclization Approach Spessard, S. J.; Stoltz, B. M. Org. Lett. 2002, 4, Simpkins Syntheses of (±)-Clusianone, (±)-Garsubellin A, and (±)-Nemorosone Rodeschini, V.; Ahmad, N. M.; Simpkins, N. S. Org. Lett. 2006, 8, Ahmad, N. M.; Rodeschini, V.; Simpkins, N. S.; Ward, S. E.; Blake, A. J. J. Org. Chem. 2007, 72, Simpkins, N. S.; Taylor, J. D.; Weller, M. D.; Hayes, C. J. Synlett 2010,
6 Part 2. Synthetic Strategies towards bicyclo[3.3.1]nonane Porco s Biomimetic Synthesis: Dearomatization / Annulation Strategy Qi, J.; Porco, J. A. Jr. J. Am. Chem. Soc. 2007, 129, Qi, J.; Beeler, A. B.; Zhang, Q.; Porco, J. A. Jr. J. Am. Chem. Soc. 2010, 132,
7 Part 2. Synthetic Strategies towards bicyclo[3.3.1]nonane Porco s Biomimetic Synthesis: Dearomatization / Annulation Strategy Qi, J.; Porco, J. A. Jr. J. Am. Chem. Soc. 2007, 129, Qi, J.; Beeler, A. B.; Zhang, Q.; Porco, J. A. Jr. J. Am. Chem. Soc. 2010, 132,
8 Part 2. Synthetic Strategies towards bicyclo[3.3.1]nonane Miscellaneous Synthetic Strategies 1999, Nicolaou s Selenium-mediated Cyclization 2002, Young s Intramolecular [3+2] Cycloaddition 2005, Barriault s Cationic Cyclization Cascade Nicolaou, K. C.; Pfefferkorn, J. A.; Kim, S.; Wei, H. X. J. Am. Chem. Soc. 1999, 121, Young, D. G. J.; Zeng, D. J. Org. Chem. 2002, 67, Lavigne, R. M. A.; Riou, M.; Girardin, M.; Morency, L.; Barriault, L. Org. Lett. 2005, 7,
9 Part 2. Synthetic Strategies towards bicyclo[3.3.1]nonane Miscellaneous Synthetic Strategies 2005, Shibasaki s Ring-Closing Metathesis Strategy 2009, Barriault s Gold-Catalyzed 6-endo-dig Cyclization 2010, Nakata s Intramolecular Cyclopropanation/Fragmentation Approach Kuramochi, A.; Usuda, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, Mitasev, B.; Be tournay, G.; Bellavance, G.; Barriault, L. Org. Lett. 2009, 11, Abe, M.; Saito, A.; Nakata, M. Tetrahedron Lett. 2010, 51,
10 Part 2. Synthetic Strategies towards bicyclo[3.3.1]nonane Summary Richard, J.-A.; Pouwer, R. H.; Chen, D. Y.-K. Angew. Chem. Int. Ed. 2012, 51,
11 Part 3. Introduction of Hyperforin Isolated from Hypericum perforatum (St. John s wort) in 1971; Structure disclosed in 1975; Responsible for antidepressant activity of the herb (St. John s wort) Mechanism: block the re-uptake of a variety of neurotransmitters by selectively activating TRPC6 (classical transient receptor potential protein), which leads to a cellular influx of Na + and Ca 2+, diminishing membrane electrochemical gradient (indirectly inhibiting neuronal neurotransmitter reuptake) and triggering cell differentiation; Anti-bacterial activity against multi-resistant Staphylococcus aureus and other Gram-positive bacteria; Highly oxidized bicyclo[3.3.1]nonane core; Densely substituted with terpenoid side chains; 5 total syntheses by Shibasaki (2010), Nakata (2013), Shair (2013), Barriault (2014), Maimone (2015), respectively. Hypericum perforatum (St. John s wort) Biosynthesis (Stage 2) 11
12 Part 4. Shibasaki s Total Synthesis of ent-hyperforin Professor Masakatsu Shibasaki Biography: 1974: University of Tokyo, Ph.D. Research advisor: Prof. Shun-ichi Yamada : Harvard University, Post-doctoral fellow Research advisor: Prof. E. J. Corey 柴崎正勝 Research Interests: Asymmetric Catalysis Total Synthesis Drug Design : Teikyo University, Associate Professor (Prof. Shiro Ikegami) : Sagami Chemical Research Center, Research group leader : Hokkaido University, Professor : University of Tokyo, Professor 2010-present: University of Tokyo/Hokkaido University, Professor Emeritus Publications and Citations: 512 publications ( ) 1 Science, 98 JACS, 31 ACIE, 3985 citations for asymmetric catalysis ( ) Noyori (2533), Hayashi (2452), Jacobsen (2449), Trost (2291) (Source: Thomson) 12
13 Part 4. Shibasaki s Total Synthesis of ent-hyperforin Claisen Rearrangement / RCM Approach Kuramochi, A.; Usuda, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, Shimizu, Y.; Shi, S.-L.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. Int. Ed. 2010, 49, Shimizu, Y.; Shi, S.-L.; Usuda, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2010, 66,
14 Part 4. Shibasaki s Total Synthesis of Hyperforin Claisen Rearrangement / RCM Approach Shimizu, Y.; Shi, S.-L.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. Int. Ed. 2010, 49, Shimizu, Y.; Shi, S.-L.; Usuda, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2010, 66,
15 Part 4. Shibasaki s Total Synthesis of Hyperforin Claisen Rearrangement / Aldol Approach Shimizu, Y.; Shi, S.-L.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. Int. Ed. 2010, 49, Shimizu, Y.; Shi, S.-L.; Usuda, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2010, 66,
16 Part 4. Shibasaki s Total Synthesis of Hyperforin Claisen Rearrangement / Aldol / Pummerer Approach 7-step synthesis of steps Tedious redox procedures and protection/deprotection processes Cross metathesis Pummerer rearrangement First total synthesis Enantioselective Shimizu, Y.; Shi, S.-L.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. Int. Ed. 2010, 49, Shimizu, Y.; Shi, S.-L.; Usuda, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2010, 66,
17 Part 5. Nakata s Total Synthesis of Hyperforin Professor Masahisa Nakata Biography: 1982: University of Tokyo, B.S : University of Tokyo, M.S : University of Tokyo, Assistant Professor, Ph.D. Research advisor: Prof. Masaji Ohno : University of Tokyo, Post-doctoral fellow Research advisor: Prof. Masakatsu Shibasaki : The Scripps Research Institute, Post-doctoral fellow Research advisor: Prof. K. C. Nicolaou 中田雅久 Research Interests: Total Synthesis Synthetic Methodology Chemical Biology : Waseda University, Associate Professor 2000-present: Waseda University, Professor Publications: 144 publications (1988-present) 9 JACS, 7 ACIE 17
18 Part 5. Nakata s Total Synthesis of Hyperforin Intramolecular Cyclopropanation / Fragmentation Approach Abe, M.; Saito, A.; Nakata, M. Tetrahedron Lett. 2010, 51, Nemorosone: Uwamori, M.; Saito, A.; Abe, M.; Nakata, M. J. Org. Chem. 2012, 77, Uwamori, M.; Nakata, M. Tetrahedron Lett. 2013, 54,
19 Part 5. Nakata s Total Synthesis of Hyperforin Intramolecular Cyclopropanation / Fragmentation Approach Uwamori, M.; Nakata, M. Tetrahedron Lett. 2013, 54,
20 Part 5. Nakata s Total Synthesis of Hyperforin Intramolecular Cyclopropanation / Fragmentation Approach 35-step LLS Cyclopropanation More efficient cross metathesis Less efficient Wittig homologation Racemic total synthesis Could be enantioselective Uwamori, M.; Nakata, M. Tetrahedron Lett. 2013, 54,
21 Part 6. Shair s Total Synthesis of Hyperforin Professor Matthew Shair Biography: : University of Rochester, B.S. with distinction : Yale University, M.S : Columbia University, Ph.D. Research advisor: Prof. S. J. Danishefsky : Harvard University, Post-doctoral fellow Research advisor: Prof. S. L. Schreiber : Harvard University, Assistant Professor : Harvard University, Associate Professor 2002-present: Harvard University, Professor Research Interests: Cancer Biology Chemical Biology Total Synthesis Publications: 37 publications (Independent career) 1 Nature, 18 JACS, 3 ACIE 21
22 Part 6. Shair s Total Synthesis of Hyperforin Biomimetic Cyclization Approach Sparling, B. A.; Moebius, D. C.; Shair, M. D. J. Am. Chem. Soc. 2013, 135,
23 Part 6. Shair s Total Synthesis of Hyperforin Biomimetic Cyclization Approach Sparling, B. A.; Moebius, D. C.; Shair, M. D. J. Am. Chem. Soc. 2013, 135,
24 Part 6. Shair s Total Synthesis of Hyperforin Biomimetic Cyclization Approach 18-step LLS Efficient Biomimetic Cyclization Enantioselective Sparling, B. A.; Moebius, D. C.; Shair, M. D. J. Am. Chem. Soc. 2013, 135,
25 Part 7. Barriault s Total Synthesis of Hyperforin Professor Louis Barriault Biography: 1993: University of Sherbrooke, B.S : University of Sherbrooke, Ph.D. Research advisor: Prof. Pierre Deslongchamps : Ohio State University, Post-doctoral fellow Research advisor: Prof. L. A. Paquette : University of Ottawa, Assistant Professor 2010-present: University of Ottawa, Full Professor Research Interests: Gold Catalysis Total Synthesis Publications: 50 publications (1997-present) 1 Nature, 3 JACS, 4 ACIE 25
26 Part 7. Barriault s Total Synthesis of Hyperforin Au-Catalyzed Cyclization Approach Mitasev, B.; Be tournay, G.; Bellavance, G.; Barriault, L. Org. Lett. 2009, 11, Bellavance, G.; Barriault, L. Angew. Chem. Int. Ed. 2014, 53,
27 Part 7. Barriault s Total Synthesis of Hyperforin Au-Catalyzed Cyclization Approach 17-step LLS Highly Efficient Cyclization Problematic late-stage functionalzaition Bellavance, G.; Barriault, L. Angew. Chem. Int. Ed. 2014, 53,
28 Part 8. Maimone s Total Synthesis of Hyperforin Professor Thomas Maimone Biography: : University of California, Berkeley, B.S. Research advisor: Prof. Dirk Trauner : The Scripps Research Institute, Ph.D. Research advisor: Prof. P. S. Baran : MIT, NIH Post-doctoral fellow Research advisor: Prof. S. L. Buchwald 2012-present: University of California, Berkeley Assistant Professor Research Interests: Total Synthesis Publications: 17 publications (2000-present) 2 Nature, 8 JACS, 4 ACIE 4 publications (Independent career) 2 JACS, 2 ACIE 28
29 Part 8. Maimone s Total Synthesis of Hyperforin Polarity-reverse C-C Bond Formation Approach Daum, S. J. Tetrahedron Lett. 1984, 25, Ting, C. P.; Maimone, T. J. J. Am. Chem. Soc. 2015, 137,
30 Part 8. Maimone s Total Synthesis of Hyperforin Polarity-reverse C-C Bond Formation Approach 10-step LLS Ting, C. P.; Maimone, T. J. J. Am. Chem. Soc. 2015, 137,
31 Summary 31
32 Summary 32
33 Thank you for your attention! 33
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