Build/couple/pair strategy for the synthesis of stereochemically diverse macrolactams via head-to-tail cyclization

ACS Combinatorial Science

Volumn 14, Issue 2, 2012, Pages 89-96

  Fitzgerald, Mark E ^a   Mulrooney, Carol A ^a   Duvall, Jeremy R ^a   Wei, Jingqiang ^a   Suh, Byung Chul ^a   Akella, Lakshmi B ^a   Vrcic, Anita ^a   Marcaurelle, Lisa A ^a,b  

^a BROAD INSTITUTE OF MIT AND HARVARD   (United States)

^b EISAI INC   (United States)

Author keywords

diversity oriented synthesis; macrocycle; solid phase synthesis; stereochemistry

Indexed keywords

MACROCYCLIC LACTAM;

ARTICLE; CHEMISTRY; CYCLIZATION; METHODOLOGY; SOLID PHASE SYNTHESIS; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; LACTAMS, MACROCYCLIC; SOLID-PHASE SYNTHESIS TECHNIQUES; STEREOISOMERISM;

EID: 84856936324     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co200161z     Document Type: Article

References (26)

1. Marcaurelle, L. A.; Comer, E.; Dandapani, S.; Duvall, J. R.; Gerard, B.; Kesavan, S.; Lee, M. D.; Liu, H.; Lowe, J. T.; Marie, J.-C.; Mulrooney, C. A.; Pandya, B. A.; Rowley, A.; Ryba, T. D.; Suh, B.-C.; Wei, J.; Young, D. W.; Akella, L. B.; Ross, N. T.; Zhang, Y.-L.; Fass, D. M.; Reis, S. A.; Zhao, W.-N.; Haggarty, S. J.; Palmer, M.; Foley, M. A. An aldol-based build/couple/pair strategy for the synthesis of medium- and large-sized rings: discovery of macrocyclic histone deacetylase inhibitors J. Am. Chem. Soc. 2010, 132, 16962-16976
2. Comer, E.; Liu, H.; Joliton, A.; Claubat, A.; Johnson, C.; Akella, L. B.; Marcaurelle, L. A. Fragment-based domain shuffling approach for the synthesis of pyran-based macrocycles Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 6751-6756
3. Kelly, A. R.; Wei, J.; Kesavan, S.; Marie, J. C.; Windmon, N.; Young, D. W.; Marcaurelle, L. A. Accessing skeletal diversity using catalyst control: formation of n and n + 1 macrocyclic triazole rings Org. Lett. 2009, 11, 2257-2260
4. NAr cycloetherification ACS Comb. Sci. 2011, 13, 365-374
5. Lovering, F.; Bikker, J.; Humblet, C. Escape from flatland: increasing saturation as an approach to improving clinical success J. Med. Chem. 2009, 52, 6752-6756
6. Driggers, E. M.; Hale, S. P.; Lee, J.; Terrett, N. K. The exploration of macrocycles for drug discovery: An underexploited structural class Nat. Rev. Drug Discovery 2008, 7, 608-624 (Pubitemid 351927725)
7. Drahl, C. Big hopes ride on big rings Chem. Eng. News 2009, 87, 54-57
8. Pal, S. A journey across the sequential development of macrolides and ketolides related to erythromycin Tetrahedron 2006, 62, 3171-3200
9. Lee, F.; Borzilleri, R.; Fairchild, C.; Kamath, A.; Smykla, R.; Kramer, R.; Vite, G. Preclinical discovery of ixabepilone, a highly active antineoplastic agent Cancer Chemother. Pharmacol. 2008, 63, 157-166
10. Marsault, E.; Peterson, M. L. Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery J. Med. Chem. 2011, 54, 1961-2004
11. Tyndall, J. D. A.; Fairlie, D. P. Macrocycles mimic the extended peptide conformation recognized by aspartic, serine, cysteine and metallo proteases Curr. Med. Chem. 2001, 8, 893-907 (Pubitemid 32633548)
12. Wessjohann, L. A.; Ruijter, E.; Garcia-Rivera, D.; Brandt, W. What can a chemist learn from nature's macrocycles?-a brief, conceptual view Mol. Diversity 2005, 9, 171-186 (Pubitemid 40394851)
13. Nielsen, T. E.; Schreiber, S. L. Towards the optimal screening collection: a synthesis strategy Angew. Chem., Int. Ed. 2008, 47, 48-56
14. Schreiber, S. L. Organic chemistry: Molecular diversity by design Nature 2009, 457, 153-154 and references sited therein.
15. Pandya, B. A.; Dandapani, S.; Duvall, J. R.; Rowley, A.; Mulrooney, C. A.; Ryba, T; Dombrowski, M.; Harton, M.; Young, D. W.; Marcaurelle, L. A. Practical asymmetric synthesis of β-hydroxy γ-amino acids via complimentary aldol reactions Tetrahedron 2011, 67, 6131-6137
16. Zhang, Q.; Lu, H.; Richard, C.; Curran, D. P. Fluorous mixture synthesis of stereoisomer libraries: Total syntheses of (+)-murisolin and fifteen diastereoisomers J. Am. Chem. Soc. 2004, 126, 36-37 (Pubitemid 38090327)
17. Dandapani, S.; Jeske, M.; Curran, D. Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones-Tools and tactics for solving problems in fluorous mixture synthesis J. Org. Chem. 2005, 70, 9447-9462 (Pubitemid 41611701)
18. Sauer, W. H.; Schwarz, M. K. Molecular shape diversity of combinatorial libraries: a prerequisite for broad activity J. Chem. Inf. Comput. Sci. 2003, 43, 987-1003
19. NAr-based cycloetherification Tetrahedron Lett. 2003, 44, 5575-5578 (Pubitemid 36782582)
20. Temal-Lab, T.; Chastanet, J.; Zhu, J. A convergent approach to cyclopeptide alkaloids: Total synthesis of sanjoinine G1 J. Am. Chem. Soc. 2002, 124, 583-590 (Pubitemid 34101164)
21. Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Mitsunobu and related reactions: advances and applications Chem. Rev. 2009, 109, 2551-2651
22. www.mimotopes.com
23. Jensen, K. J.; Alsina, J.; Songster, M. F.; Vágner, J.; Albericio, F.; Barany, G. Backbone amide linker (BAL) strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides J. Am. Chem. Soc. 1998, 120, 5441-5452
24. Boas, U.; Brask, J.; Jensen, K. Backbone amide linker in solid-phase synthesis J. Chem. Rev. 2009, 109, 2092-2118
25. Akella, L. B.; Marcaurelle, L. A. Application of a sparse matrix design strategy to the synthesis of DOS libraries ACS Comb. Sci. 2011, 13, 365-374
26. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 2001, 46, 3-26 (Pubitemid 33653411)