Recent Progress in the Chemistry of Mucohalic Acids: Versatile Building Blocks in Organic Synthesis

Ji Zhang; Koushik Das Sarma; Timothy T. Curran

doi:10.1055/s-0032-1318138

Synlett, Table of Contents

Synlett 2013; 24(5): 550-569
DOI: 10.1055/s-0032-1318138

account

Recent Progress in the Chemistry of Mucohalic Acids: Versatile Building Blocks in Organic Synthesis

Ji Zhang*

Research API, Pfizer Global Research and Development, Ann Arbor Laboratories, Pfizer Inc., 2800 Plymouth Road, Ann Arbor, Michigan 48105, USA Fax: +86(769)85370223 Email: zhangji@hecpharm.com Email: jizhang009@yahoo.com

,

Koushik Das Sarma

Research API, Pfizer Global Research and Development, Ann Arbor Laboratories, Pfizer Inc., 2800 Plymouth Road, Ann Arbor, Michigan 48105, USA Fax: +86(769)85370223 Email: zhangji@hecpharm.com Email: jizhang009@yahoo.com

,

Timothy T. Curran

Research API, Pfizer Global Research and Development, Ann Arbor Laboratories, Pfizer Inc., 2800 Plymouth Road, Ann Arbor, Michigan 48105, USA Fax: +86(769)85370223 Email: zhangji@hecpharm.com Email: jizhang009@yahoo.com

› Author Affiliations

Abstract

All articles of this category

Dedicated to the Ann Arbor Laboratories of Parke-Davis/Pfizer where Lipitor and Lyrica were invented and developed.

Abstract

This account documents our recent progress in exposing some of the potential of mucohalic acids in synthetic applications. Understanding their stability and reactivity in different reaction media allows the development of mild and regioselective methods to access various substituted butenolides, butenolactams, and 4,5-dihalopyridazin-3(2H)-ones and to create other novel, multifunctionalized building blocks.

1 Introduction

2 The Rationale for the Reinvestigation of Mucohalic Acid Chemistry

3 Understanding the Stability of Mucohalic Acids

4 One-Pot Synthesis of a 4,5-Dihalopyridazin-3(2H)-one and the Process Chemistry of ABT-963

5 Reductive Amination of Mucochloric Acid and Synthesis of Antiseizure Drug Levetiracetam (Keppra)

6 Reduction of Mucohalic Acids and Synthesis of Anti-inflammatory Agent Rofecoxib (Vioxx)

7 Lewis Acid Catalyzed Knoevenagel Aldol Reaction

8 Lewis and Brønsted Acid Promoted Friedel–Crafts Hydroxyalkylation

9 Lewis Acid Facilitated Mukaiyama Aldol Reaction

10 Indium-Mediated Allylation in Water

11 Palladium-Free Regioselective Etherification and Amination

12 Novel Building Blocks Derived from Mucohalic Acids

13 Direct Vinylogous Aldol Addition Using α,β-Dihalo-Substituted Butenolides and Butenolactams

14 Other Applications

15 Summary and Conclusion

Key words

mucohalic acids - butenolides - γ-lactones - γ-lactams - building blocks

Full Text

References

References

1a Jackson O. Am. Chem. J. 1881; 3: 4
1b Allen C. Org. Synth. 1955; 3: 621
1c Limpricht H. Justus Liebigs Ann. Chem. 1873; 165: 253

2 Wasserman HH, Precopio FM. J. Am. Chem. Soc. 1952; 74: 326
3 Hill HB, Jackson OR. Am. Chem. J. 1890; 12: 37
4 Simonis H. Ber. Dtsch. Chem. Ges. 1899; 32: 2085
5 Dury K. Angew. Chem. 1960; 72: 864
6 Sulikowski GA, Agnelli F, Corbett RM. J. Org. Chem. 2000; 65: 337

7a Wasserman HH, Precopio FM, Lin T.-C. J. Am. Chem. Soc. 1953; 75: 2527
7b Wasserman HH, Precopio FM, Liu T.-C. J. Am. Chem. Soc. 1952; 74: 4093
7c Wasserman HH, Precopio FM. J. Am. Chem. Soc. 1954; 76: 1242

8a Mowry DT. J. Am. Chem. Soc. 1953; 75: 1909
8b Mowry DT. J. Am. Chem. Soc. 1950; 72: 2535

9a Duczek W, Jähnisch K. Synthesis 1992; 935
9b Duczek W, Jähnisch K, Kunath A, Reck G, Winter G, Schulz B. Liebigs Ann. Chem. 1992; 8: 781

10a Lattmann E, Sattayasai N, Niamsanit S, Dunn S. Bioorg. Med. Chem. Lett. 2005; 15: 919
10b Lattmann E, Sattayasai N, Schwalbe CS, Niamsanit S, Billington DC, Lattmann P, Langley CA, Singh H, Dunn S. Curr. Drug. Discovery Technol. 2006; 3: 125

11a Bellina F, Rossi R, Raugei E. Synlett 2000; 1749
11b Bellina F, Rossi R, Anselmi C. Tetrahedron Lett. 2001; 42: 3851
11c Bellina F, Rossi R, Anselmi C, Viel S, Mannina L. Tetrahedron 2001; 57: 9997
11d Bellina F, Rossi R. Synthesis 2002; 2729
11e Bellina F, Rossi R, Falchi E. Tetrahedron 2003; 59: 9091
11f Bellina F, Rossi R. Synthesis 2007; 1887

For reviews, see:

12a Cunha S, Oliveira CC. Quim. Nova 2011; 34: 1425
12b Bellina F, Rossi R. Curr. Org. Chem. 2004; 12: 1089

13a Ma S.-M, Yu Z.-Q. Org. Lett. 2003; 5: 2581
13b Ma S.-M, Duan D.-H, Shi Z.-J. Org. Lett. 2000; 2: 1419
13c Ma S.-M, Xie H.-X. Org. Lett. 2000; 2: 3801
13d Ma S.-M, Yu Z.-Q. Org. Lett. 2003; 5: 1507
13e Chen G.-F, Zeng R, Gu Z.-H, Fu C.-L, Ma S.-M. Org. Lett. 2008; 10: 4235
13f Li S.-H, Ma S.-M. Org. Lett. 2011; 13: 6046

14 Zhang J, Morton HE, Ji J. Tetrahedron Lett. 2006; 47: 8733
15 Jähnisch K, Duczek W. J. Prakt. Chem. 1990; 332: 117
16 Kerdesky FA, Leanna MR, Zhang J, Li W, Lallaman JE, Ji J, Morton HE. Org. Process Res. Dev. 2006; 10: 512

17a Lattmann E, Kinchington D, Dunn S, Singh H, Ayuko WO, Tisdale MJ. J. Pharm. Pharmacol. 2004; 56: 1163
17b Duczek W, Jähnisch K, Kunath A, Reck G, Winter G, Schulz B. Liebigs Ann. Chem. 1992; 8: 781

18a Silverman RB. J. Med. Chem. 2012; 55: 567
18b Silverman RB. Angew. Chem. Int. Ed. 2008; 47: 3500

19 Zhang J, Blazecka PG, Davidson JG. Org. Lett. 2003; 5: 553
20 Das Sarma K, Zhang J, Huang Y, Davidson JG. Eur. J. Org. Chem. 2006; 3730
21 Zhang J, Blazecka PG, Belmont D, Davidson JG. Org. Lett. 2002; 4: 4559
22 Zhang J, Das Sarma K, Curran TT, Belmont DT, Davidson JG. J. Org. Chem. 2005; 70: 5890

23a Gathergood N, Zhuang W, Jørgensen KA. J. Am. Chem. Soc. 2000; 122: 12517
23b Majer J, Kwiatkowski P, Jurczak J. Org. Lett. 2011; 13: 5944
23c Ghosh AK, Martyr CD, Xu C.-X. Org. Lett. 2012; 14: 2002

24 Zhang J, Blazecka PG, Curran TT. Tetrahedron Lett. 2007; 48: 2611
25 Angell P, Zhang J, Belmont D, Curran T, Davidson JG. Tetrahedron Lett. 2005; 46: 2029
26 Zhang J, Blazecka PG, Berven H, Belmont D. Tetrahedron Lett. 2003; 44: 5579
27 Blazecka PG, Belmont D, Curran T, Pflum D, Zhang J. Org. Lett. 2003; 5: 5015
28 Zhang J, Das Sarma K, Curran TT. Tetrahedron Lett. 2005; 46: 6433
29 Das Sarma K, Zhang J, Curran TT. J. Org. Chem. 2007; 72: 3311
30 Ube H, Shimada N, Terada M. Angew. Chem. Int. Ed. 2010; 49: 1858
31 Luo J, Wang H, Han X, Xu L.-W, Kwiatkowski J, Huang K.-W, Lu Y.-X. Angew. Chem. Int. Ed. 2011; 50: 1861
32 Guo Y.-L, Bai J.-F, Peng L, Wang L.-L, Jia L.-N, Luo X.-Y, Tian F, Xu X.-Y, Wang L.-X. J. Org. Chem. 2012; 77: 8338
33 Gomez-Paloma L, Aquino M, Bruno I. Org. Lett. 2006; 8: 4831
34 Guerrero MD, Aquino M, Bruno I, Terencio MC, Paya M, Riccio R, Gomez-Paloma L. J. Med. Chem. 2007; 50: 2176
35 Humphries P, Oliver RM. Tetrahedron Lett. 2009; 50: 2682
36 Frolov EB, Lakner FJ, Khvat AV, Ivachtchenko AV. Tetrahedron Lett. 2004; 45: 4693
37 Dyck B, Markison S, Zhao L, Tamiya J, Grey J, Rowbottom MW, Zhang M, Vickers T, Sorensen K, Norton C, Wen J, Heise CE, Saunders J, Conlon P, Madan A, Schwarz D, Goodfellow VS. J. Med. Chem. 2006; 49: 3753
38 Qian W, Winternheimer D, Allen J. Org. Lett. 2011; 13: 1682
39 O’Dwyer EE, Mullane NS, Smyth TP. J. Heterocycl. Chem. 2011; 48: 286
40 Tan Y.-H, Li J.-X, Xue F.-L, Qi J, Wang Z.-Y. Tetrahedron 2012; 68: 2827
41 Wei M.-X, Feng L, Li X.-Q, Zhou X.-Z, Shao Z.-H. Eur. J. Med. Chem. 2009; 44: 3340
42 Ren J, Ma D.-D, Sha Y, Li F, Cheng M.-S. Heterocycles 2010; 81: 1427
43 Cunha S, Oliveira CC, Sabino JR. J. Braz. Chem. Soc. 2011; 22: 598