Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2023; 55(13): 2047-2052
DOI: 10.1055/a-2016-4548
DOI: 10.1055/a-2016-4548
paper
Hexafluoroisopropanol-Induced Facial Selectivity in a Hindered Diels–Alder Reaction
This work was funded by the Slim Initiative for Genomic Medicine in the Americas (SIGMA), a collaboration of the Broad Institute with the Carlos Slim Foundation.
Abstract
BRD4780 is a small molecule that can selectively clear mutant MUC1-fs protein in mucin kidney disease models. Prior syntheses of BRD4780 were unsuitable for preparation on large scale. In this manuscript, HFIP is described as a unique solvent that allowed the key Diels–Alder reaction to proceed with >20:1 endo diastereoselectivity, enabling the kg-scale preparation of BRD4780 for further studies.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2016-4548.
- Supporting Information
Publication History
Received: 14 December 2022
Accepted after revision: 19 January 2023
Accepted Manuscript online:
19 January 2023
Article published online:
20 March 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Hubbard RD, Miller BL. J. Org. Chem. 1998; 63: 4143
- 1b Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
- 1c Corey EJ, Guzman-Perez A. Angew. Chem. Int. Ed. 1998; 37: 388
- 2 Lam Y.-h, Cheong PH.-Y, Blasco Mata JM, Stanway SJ, Gouverneur V, Houk KN. J. Am. Chem. Soc. 2009; 131: 1947
- 3 Dvela-Levitt M, Shaw JL, Greka A. Trends Mol. Med. 2021; 27: 394
- 4 Munk SA, Lai RK, Burke JE, Arasasingham PN, Kharlamb AB, Manlapaz CA, Padillo EU, Wijono MK, Hasson DW, Wheeler LA, Garst ME. J. Med. Chem. 1996; 39: 1193
- 5 Corsello SM, Bittker JA, Liu Z, Gould J, McCarren P, Hirschman JE, Johnston SE, Vrcic A, Wong B, Khan M, Asiedu J, Narayan R, Mader CC, Subramanian A, Golub TR. Nat. Med. 2017; 23: 405
- 6 Dvela-Levitt M, Kost-Alimova M, Emani M, Kohnert E, Thompson R, Sidhom EH, Rivadeneira A, Sahakian N, Roignot J, Papagregoriou G, Montesinos MS, Clark AR, McKinney D, Gutierrez J, Roth M, Ronco L, Elonga E, Carter TA, Gnirke A, Melanson M, Hartland K, Wieder N, Hsu JC, Deltas C, Hughey R, Bleyer AJ, Kmoch S, Živná M, Barešova V, Kota S, Schlondorff J, Heiman M, Alper SL, Wagner F, Weins A, Golub TR, Lander ES, Greka A. Cell 2019; 178: 521-535.e23
- 7 Takenaka N, Sarangthem RS, Seerla SK. Org. Lett. 2007; 9: 2819
- 8 Wittkopp A, Schreiner PR. Chem. Eur. J. 2003; 9: 407
- 9 Denmark SE, Cramer CJ, Sternberg JA. Helv. Chim. Acta 1986; 69: 1971
- 10 Denmark SE, Moon YC, Senanayake CB. W. J. Am. Chem. Soc. 1990; 112: 311
- 11 Çelebi-Ölçüm N, Ess DH, Aviyente V, Houk KN. J. Am. Chem. Soc. 2007; 129: 4528
- 12 Ruiz-Lopez MF, Assfeld X, Garcia JI, Mayoral JA, Salvatella L. J. Am. Chem. Soc. 1993; 115: 8780
- 13 Cativiela C, García JI, Mayoral JA, Salvatella L. Can. J. Chem. 1994; 72: 308
- 14 Cativiela C, García JI, Gil J, Martínez RM, Mayoral JA, Salvatella L, Urieta JS, Mainar AM, Abraham MH. J. Chem. Soc., Perkin Trans. 2 1997; 653
- 15 Motiwala HF, Armaly AM, Cacioppo JG, Coombs TC, Koehn KR. K, Norwood VM. IV, Aubé J. Chem. Rev. 2022; 122: 12544
- 16 Jasiński R, Koifman O, Barański A. Open Chem. 2011; 9: 1008
- 17 Yang Y.-F, Yu P, Houk KN. J. Am. Chem. Soc. 2017; 139: 18213