Total Synthesis of ( )-Nakadomarin A
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1 Total Synthesis of ( )-Nakadomarin A Pavol Jakubec, Dane M. Cockfield, and Darren J. Dixon University of Oxford and University of Manchester, UK J. Am. Chem. Soc. 2009, ASAP DOI: /ja908399s Marie-Céline Frantz Wipf Group - Current Literature November 14, 2009 Marie-Celine Wipf Group Page 1 of 14 12/28/2009
2 Nakadomarin A Isolated from the sponge Amphimedon sp. off the coast of the Kerama Islands, Okinawa, in Marine alkaloid of the manzamine family. Biological activity: Cytotoxic activity against murine lymphoma L1210 cells (IC µg/ml) Inhibition of cyclin dependent kinase 4 (IC µg/ml) Antimicrobial activity against: fungus Trichophyton mentagrophytes (MIC 23 µg/ml) Gram+ bacterium Corynebacterium xerosis (MIC 11 µg/ml) Hexacyclic structure containing: - an 8/5/5/5/15/6 ring system (1 furan) - 4 stereogenic centers (1 quaternary) Manzamine A Kobayashi, J.; Watanabe, D.; Kawasaki, N.; Tsuda, M. J. Org. Chem. 1997, 62, 9236 Kobayashi, J.; Tsuda, M.; Ishibashi, M. Pure Appl. Chem. 1999, 71, 1123 Marie-Celine Wipf Group Page 2 of 14 12/28/2009
3 Nakadomarin A synthesis Methodologies targeting the core of nakadomarin A Fürstner (Max Planck) 1999: alkyne RCM/semireduction (CF rings) Fürstner (Max Planck) 2001: olefin RCM (ADE rings) Magnus (Univ. Texas) 2002: Pauson-Khand (ABC rings) Tius (Univ. Hawaii) 2003: Nazarov (BC rings) Williams (Colorado State Univ.) 2004: azomethine ylide [1,3]-dipolar cycloaddition (ADE rings) Kerr (Univ. West. Ontario) 2005: nitrone/cyclopropane cycloaddition (ABCD rings) Funk (Penn. State Univ.) 2006: Michael/N-acyliminium ion cyclization (ABCD rings) Zhai (Shangai Institute) 2008: Sonogashira, Pt(II)-cat. cyclizations, Barton- McComble (ABCD rings) 2 total syntheses of the antipode (+)-Nakadomarin A Nishida (Chiba Univ.) 2003: 37 steps (longest linear sequence) Kerr (Univ. West. Ontario) 2007: 29 steps (longest linear sequence) 1 total synthesis of ( )-Nakadomarin A Nishida (Chiba Univ.) 2004: 36 steps (longest linear sequence) Marie-Celine Wipf Group Page 3 of 14 12/28/2009
4 Nishida synthesis of (+)-Nakadomarin A (2003) Longest linear sequence: 37 steps Nagata, T.; Nakagawa, M.; Nishida, A. J. Am. Chem. Soc. 2003, 125, 7484 Marie-Celine Wipf Group Page 4 of 14 12/28/2009
5 Nishida synthesis of ( )-Nakadomarin A (2004) Longest linear sequence: 36 steps Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem. Int. Ed. 2004, 43, 2020 Marie-Celine Wipf Group Page 5 of 14 12/28/2009
6 Kerr synthesis of (+)-Nakadomarin A (2007) Longest linear sequence: 29 steps Young, I. S.; Kerr, M. A. J. Am. Chem. Soc. 2007, 129, 1465 Marie-Celine Wipf Group Page 6 of 14 12/28/2009
7 Title paper: Retrosynthesis Jakubec, P.; Cockfield, D. M.; Dixon, D. J. J. Am. Chem. Soc. 2009, ASAP Marie-Celine Wipf Group Page 7 of 14 12/28/2009
8 Enantioselective Michael addition Cinchona alkaloid derivatives: Bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes Proposed pretransition state assembly: binding of nitro-alkene to catalyst 2 Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481 McCooey, S. H.; Connon, S. J. Angew. Chem. Int. Ed. 2005, 44, 6367 Marie-Celine Wipf Group Page 8 of 14 12/28/2009
9 3-Component nitro-mannich/lactamization cascade Nitro-Mannich/lactamization cascade of γ-nitro esters with cyclic imines Jakubec, P.; Halliwell, M.; Dixon, D. J. Org. Lett. 2008, 10, 4267 Marie-Celine Wipf Group Page 9 of 14 12/28/2009
10 Applications of Michael/nitro-Mannich/lactamization sequence Enantio- and diastereoselective, one-pot, 3-component Michael/nitro-Mannich/ lactamization sequence Jakubec, P.; Halliwell, M.; Dixon, D. J. Org. Lett. 2008, 10, 4267 Formal synthesis of (3S,4R)-paroxetine Hynes, P.; Stupple, P. A.; Dixon, D. J. Org. Lett. 2008, 10, 1389 Marie-Celine Wipf Group Page 10 of 14 12/28/2009
11 Title paper: Synthesis of the Pro-Nucleophilic Fragment Intramolecular Julia-Kocienski olefination: Unprecedented highly diastereoselective formation of a (Z)-alkene in an 8-membered ring Jakubec, P.; Cockfield, D. M.; Dixon, D. J. J. Am. Chem. Soc. 2009, ASAP Marie-Celine Wipf Group Page 11 of 14 12/28/2009
12 Title paper: Synthesis of the Electrophilic Fragment Jakubec, P.; Cockfield, D. M.; Dixon, D. J. J. Am. Chem. Soc. 2009, ASAP Marie-Celine Wipf Group Page 12 of 14 12/28/2009
13 Title paper: End Play to ( )-Nakadomarin A Jakubec, P.; Cockfield, D. M.; Dixon, D. J. J. Am. Chem. Soc. 2009, ASAP Marie-Celine Wipf Group Page 13 of 14 12/28/2009
14 Conclusion and Perspectives Short and highly stereoselective total synthesis of ( )-Nakadomarin A Longest linear sequence: 12 steps (from pyroglutamol tosylate), 16 steps in total Previous total syntheses: average of 34 steps Total of 100 mg of compound prepared (8.5 mg available so far from extraction and synthesis) Key steps (Z)-selective intramolecular Julia-Kocienski olefination to form an 8-membered ring Diastereoselective nitro-olelfin Michael addition with bifunctional cinchonine catalyst Three-component nitro-mannich/lactamization cascade Diastereoselective Mannich-type furan/iminium ion cyclization (Z)-selective RCM in the presence of protonated amines Perspectives: synthesis of natural product analogs Marie-Celine Wipf Group Page 14 of 14 12/28/2009
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