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Total Synthesis of the Polycyclic Total Synthesis of the Polycyclic Total Synthesis of the Polycyclic Total Synthesis of the Polycyclic Fungal Metabolite ( Fungal Metabolite () g g ( ) ( ) )-Communesin F Communesin F Liu, P.; Seo, J.

  1. Total Synthesis of the Polycyclic Total Synthesis of the Polycyclic Total Synthesis of the Polycyclic Total Synthesis of the Polycyclic Fungal Metabolite ( Fungal Metabolite (±) g g ( ) ( ) )-Communesin F Communesin F Liu, P.; Seo, J. H.; Weinreb, S. M. Li Li Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem. Int. Ed P S P S J H W i J H W i b S M b S M A Angew. Chem. Int. Ed . A Ch Ch I I Ed Ed 2010 . 2010 2010 , 2010 49 , 49 49 2000 49 , 2000 , 2000–2003. 2000 2003 2003 2003. Me O Me Me H H N H N NH N Me Current Literature Presentation Current Literature Presentation March 6 th th , 2010 March 6 , 2010 Michael Yang Michael Yang Mi h Mi h l Y l Y Mike Yang @ Wipf Group Page 1 of 19 4/26/2010

  2. Isolation of Communesin F Isolation of Communesin F f � Isolated from Penicillium mold on marine algae Isolated from Penicillium mold on marine algae Penicillium expansum enicillium expansum Enteromorpha interstinalis Enteromorpha interstinalis Kerzaon, I.; Pouchus, Y. F.; Monteau, F.; Le Bizec, B.; Nourrisson, M. R. Rapid Commun. Mass Spectrom. 2009 , 23 , 3928. Mike Yang @ Wipf Group Page 2 of 19 4/26/2010

  3. Communesin Background Communesin Background Communesin Background Communesin Background � Biological Activities: Biological Activities: Communesins A − D are active against � various leukemia cell lines Communesins D − F are insecticidal � � Key Structural Features � Two contiguous quaternary centers (C-7 and C-8) � Two aminals Two aminals Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem. Int. Ed. 2010 , early view. Mike Yang @ Wipf Group Page 3 of 19 4/26/2010

  4. Biosynthetic Proposal 1: Biosynthetic Proposal 1: Oxidative Dimerization of Tryptamine Oxidative Dimerization of Tryptamine Wigley, L. J.; Mantle, P. G.; Perry, D. A. Phytochemistry 2006 , 67 , 561–569. Mike Yang @ Wipf Group Page 4 of 19 4/26/2010

  5. Biosynthetic Proposal 2: Biosynthetic Proposal 2: Dimerization of Tryptamine and Aurantioclavine Dimerization of Tryptamine and Aurantioclavine � Oxidative dimerization between tryptamine and aurantioclavine O id ti di i ti b t t t i d ti l i � Aurantioclavine – Penicillium fungal metabolite May, J. A.; Stoltz, B. Tetrahedron 2006 , 62 , 5262–5271. Mike Yang @ Wipf Group Page 5 of 19 4/26/2010

  6. Biosynthetic Proposal 3: Biosynthetic Proposal 3: Diels Diels- -Alder Reaction Alder Reaction May, J. A.; Zeidan, R. K.; Stoltz, B. Tetrahedron Lett. 2003 , 44 , 1203–1205. May, J. A.; Stoltz, B. Tetrahedron 2006 , 62 , 5262–5271. Mike Yang @ Wipf Group Page 6 of 19 4/26/2010

  7. Model Study: Model Study: y Communesin via Diels Communesin via Diels- -Alder Alder Cl Me Me Me Me Boc H H TsHN NH NH N Cs 2 CO 3 CH 2 Cl 2 Cs 2 CO 3 , CH 2 Cl 2 -78 °C + NTs NTs 89% (2:1 d.r.) N N N H H Me Me Me Mg, Mg NH 4 Cl, MeOH, 80% Me Me Me Me H H NH NH + NH NH N N H H Me Me May, J. A.; Zeidan, R. K.; Stoltz, B. Tetrahedron Lett. 2003 , 44 , 1203–1205. May, J. A.; Stoltz, B. Tetrahedron 2006 , 62 , 5262–5271. Mike Yang @ Wipf Group Page 7 of 19 4/26/2010

  8. Retrosynthetic Analysis Retrosynthetic Analysis - Qin Qin Me HO O Me Me Me Me H H O R N N H N NH NH N N N R Me Me O O O Br Br Br O N 2 N N 3 N N H R Me Yang, J.; Wu, H.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2007 , 129 , 13794–13795. Mike Yang @ Wipf Group Page 8 of 19 4/26/2010

  9. Diastereomers? Diastereomers? Br OH 1) SOCl 2 2) Et 3 N, CH 2 Cl 2 , 95% (2 steps) O Br N 3) TsNHNH 2 , TsOH, 85% H O 4) DBU, CH 2 Cl 2 , 85% + + N 2 N 2 N 3 N O H HO O CuOTf, N 3 CH Cl CH 2 Cl 2 , 88% O O Ar O H O O O Br H Br Br Ar + N 3 N N N Me Me Me 1 6 1.6 : : 1 1 1.6:1 d.r. Yang, J.; Wu, H.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2007 , 129 , 13794–13795. Mike Yang @ Wipf Group Page 9 of 19 4/26/2010

  10. Cyclopropane Ring Cyclopropane Ring- -opening opening O O O O Br Br PBu 3 N 3 N 3 NH NH aq. THF THF N N 83% single diastereomer Me Me PBu 3 , proton aq. THF aq THF transfer transfer O O O O O O Br Br Br NH 2 NH 2 NH 2 N N N Me Me Me Yang, J.; Wu, H.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2007 , 129 , 13794–13795. Mike Yang @ Wipf Group Page 10 of 19 4/26/2010

  11. Qin’s Mechanistic Rationale Qin’s Mechanistic Rationale Q Q M M R R Yang, J.; Song, H.; Xiao, X.; Wang, J.; Qin, Y. Org. Lett. 2006 , 8 , 2187–2190. Mike Yang @ Wipf Group Page 11 of 19 4/26/2010

  12. Formation of the C Formation of the C-8 Quaternary Center: Formation of the C Formation of the C 8 Quaternary Center: 8 Quaternary Center: 8 Quaternary Center: Claisen Rearrangement Claisen Rearrangement Yang, J.; Wu, H.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2007 , 129 , 13794–13795. Mike Yang @ Wipf Group Page 12 of 19 4/26/2010

  13. Synthesis of Communesin F Synthesis of Communesin F - Qin Qin Me Me Me 1) DMP 1) DMP H O 2) NH 2 OH·HCl, Na 2 CO 3 N O CHO Boc H HO HO 1) NH 2 OH·HCl, Na 2 CO 3 O 3) H 2 , Raney-Ni N O Br NH Br 2) H 2 , Raney-Ni, (87%, 2 steps, brsm) 4) Boc 2 O, Na 2 CO 3 3) MeONa, MeOH, 70 ° C, 98% 50% - 4 steps N N N N 5) Pd(OA ) 5) Pd(OAc) 2 , P( o -Tol) 3 , P( T l) N N N CO 2 Me CO 2 Me 68% Me Me N CO 2 Me Me Me Me HO PPTS, , CHCl 3 66% Me 1) silica gel, MeOH/CH 2 Cl 2 , Me Me OEt O Me Me 81% - 2 steps Me N N H H Boc Boc H H H H Me Me 2) KOH, MeOH/H 2 O, 65% 2) KOH M OH/H O 65% NH NH O O N H 1) BF 4 OEt 3 , iPrNEt 2 , 95% N N N 3) NaBH 4 , AcOH/Ac 2 O, 73% 2) 5% TFA, CH 2 Cl 2 N NH N N CO 2 Me N N N CO Me CO 2 Me M Me Me Me Communesin F Yang, J.; Wu, H.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2007 , 129 , 13794–13795. Mike Yang @ Wipf Group Page 13 of 19 4/26/2010

  14. Retrosynthetic Analysis Retrosynthetic Analysis - Weinreb Weinreb Me HO O Me Me Me Me H O H R Boc O N N H NH N N BOMO NH N NBoc N N N R Me Me Me CO 2 Et CO 2 Et NO 2 N BOMO BOMO N N BOMO BOMO I NO 2 O N O N Me Me Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem. Int. Ed. 2010 , 49 , 2000–2003. Mike Yang @ Wipf Group Page 14 of 19 4/26/2010

  15. Intramolecular Heck Intramolecular Heck - Weinreb Weinreb 1) LiOH, H 2 O, MeOH, 86% B(OH) 2 2) SOCl 2 ; iPr 2 NEt, 87% NO 2 BOMO N Bn Bn BOMO I N EtO N Bn Bn [Pd(PPh ) ] DME [Pd(PPh 3 ) 4 ], DME, I NO 2 H 2 O, Na 2 CO 3 NH 2 O NO 2 EtO 98% N O O OTf H 1) ClCO 2 Et, CH 2 Cl 2 , 96% 2) NaH, THF, MeI, 92% CO 2 Et CO Et CO 2 Et NO 2 N BOMO BOMO N Pd(OAc) 2 , PPh 3 , DMA, K 2 CO 3 , I NO 2 n Bu 4 NBr, 150 °C, 90% O N N N N O O Me Me Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem. Int. Ed. 2010 , 49 , 2000–2003. Mike Yang @ Wipf Group Page 15 of 19 4/26/2010

  16. 1,3 Dipolar Cycloaddition 1,3 Dipolar Cycloaddition - Weinreb Weinreb CO 2 Et CO 2 Et EtO 2 C NO 2 NHBoc N N a) 5% Pt/C, H 2 (40 atm), PhMe BOMO N BOMO BOMO b) Boc 2 O, K 2 CO 3 , THF, H 2 O, AlH 3 ·Me 2 NEt, THF 74% 87% (2 steps) O O NBoc N N N Me Me Me 1M KOH, EtOH 94 °C NC CN N NH N N BOMO BOMO HN HN BOMO O O HN HN H 93% (2 steps) N NCN 3 , MeCN OBOM N NBoc NBoc N N N N Boc Me Me Me Me Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem. Int. Ed. 2010 , 49 , 2000–2003. Mike Yang @ Wipf Group Page 16 of 19 4/26/2010

  17. Formation of C Formation of C- -8 Quaternary Center 8 Quaternary Center NC Boc N Boc O KO t Bu, N BOMO HN BOMO N O allyl iodide 1) 1M KOH, EtOH, 94 °C, 60% H OBOM THF, − 78 C THF 78 °C 2) Boc 2 O, LiHMDS, THF, 95% 2) Boc O LiHMDS THF 95% NBoc NBoc 87% N N N N Me Boc Me Me 3:1 mixture of epimers 1) 1M KOH, EtOH, 80 °C, 94% OMs 2) OsO 4 , NMO, THF, H 2 O; O OMs a) Pearlman's catalyst Boc Boc O O O O NaIO 4 NaIO HN O H 2 , THF N BOMO HN 3) NaBH 4 , EtOH BOMO b) DMP, CH 2 Cl 2 4) MsCl, NEt 3 , CH 2 Cl 2 , 0 °C, 75% (2 steps) 83% (3 steps) NBoc NBoc NBoc N N N Me Me Me Me Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem. Int. Ed. 2010 , 49 , 2000–2003. Mike Yang @ Wipf Group Page 17 of 19 4/26/2010

  18. Qin’s Intermediate Qin’s Intermediate 1) Me 2 CO, 10% NaOH/H 2 O, Me OMs OMs N 3 N 3 N 3 N 3 60 °C, 93% 60 °C 93% O O O O Boc O 2) Boc 2 O, LiHMDS, THF, NaN 3 , DMF, HN O HN N O 81% 90 °C, 61% NBoc NBoc NBoc N N N N N N Me Me Me PMe 3 , THF, H 2 O, 70 °C, 88% , Me Me Me Me O Me H Boc HO Boc H Boc H O O O HO N N N MeLi, THF, NH NH NH -78 °C, 73% N NBoc NBoc N N N CO 2 Me Me Me Me Qin's Intermediate Qin s Intermediate Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem. Int. Ed. 2010 , 49 , 2000–2003. Mike Yang @ Wipf Group Page 18 of 19 4/26/2010

  19. Summary Summary Summary Summary Qin Weinreb C-7 Quaternary Center Cyclopropanation Heck C 8 Q C-8 Quaternary Center t C t Cl i Claisen rearrangement t Enolate alkylation E l t lk l ti Overall yield 3% 1% Steps 23 30 Mike Yang @ Wipf Group Page 19 of 19 4/26/2010

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