Recent Developments in Polyene Cyclizations and Their Applications in Natural Product Synthesis

Anthony G. M. Barrett; Tsz-Kan Ma; Thomas Mies

doi:10.1055/s-0037-1610382

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(01): 67-82
DOI: 10.1055/s-0037-1610382

short review

Copyright with the author

Recent Developments in Polyene Cyclizations and Their Applications in Natural Product Synthesis

Authors

Anthony G. M. Barrett *

Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London, W12 0BZ, UK Email: agmb@ic.ac.uk
Tsz-Kan Ma
Thomas Mies

Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Cascade polyene cyclization reactions are highly efficient and elegant bioinspired transformations that involve simultaneous multiple bond constructions to rapidly generate complex polycyclic molecules. This review summarizes the most prominent work on a variety of cationic and radical cascade cyclizations and their applications in natural product synthesis published between 2014 and 2018.

1 Introduction

2 Cationic Polyene Cyclizations

2.1 Lewis Acid Mediated Polyene Cyclizations

2.2 Brønsted Acid Mediated Polyene Cyclizations

2.3 Halogen Electrophile Initiated Polyene Cyclizations

2.4 Sulfur Electrophile Initiated Polyene Cyclizations

2.5 Transition-Metal-Mediated Cationic Polyene Cyclizations

3 Radical Polyene Cyclizations

3.1 Transition-Metal-Mediated Radical Polyene Cyclizations

3.2 Photocatalyst-Mediated Polyene Cyclizations

4 Origin of Stereocontrol in Polyene Cyclizations

5 Conclusion

Key words

polyene cyclization - cascade reaction - carbon–carbon bond formation - natural products - total synthesis

Full Text

References

References

1a Stork G, Burgstahler AW. J. Am. Chem. Soc. 1955; 77: 5068
1b Eschenmoser A, Ruzicka L, Jeger O, Arigoni D. Helv. Chim. Acta 1955; 38: 1890
1c Eschenmoser A, Arigoni D. Helv. Chim. Acta 2005; 88: 3011

2a Johnson WS, Semmelhack MF, Sultanbawa MU. S, Dolak LA. J. Am. Chem. Soc. 1968; 90: 2994
2b Johnson WS. Acc. Chem. Res. 1968; 1: 1
2c Johnson WS. Bioorg. Chem. 1976; 5: 51

3a van Tamelen EE. Acc. Chem. Res. 1968; 1: 111
3b van Tamelen EE. Acc. Chem. Res. 1975; 8: 152

For recent reviews in this area, see

4a Snyder SA, Levinson AM. Comprehensive Organic Synthesis II . Vol. 3. Elsevier; Oxford: 2014: 268
4b Li X.-W, Nay B. Nat. Prod. Rep. 2014; 31: 533
4c Felix RJ, Munro-Leighton C, Gagné MR. Acc. Chem. Res. 2014; 47: 2319
4d Yoshimura T. Tetrahedron Lett. 2014; 55: 5109
4e Dhambri S, Mohammad S, Van Buu ON, Galvani G, Meyer Y, Lannou M.-I, Sorin G, Ardisson J. Nat. Prod. Rep. 2015; 32: 841
4f Ardkhean R, Caputo DF. J, Morrow SM, Shi H, Xiong Y, Anderson EA. Chem. Soc. Rev. 2016; 45: 1557
4g Ungarean CN, Southgate EH, Sarlah D. Org. Biomol. Chem. 2016; 14: 5454
4h Hung K, Hu X, Maimone TJ. Nat. Prod. Rep. 2018; 35: 174
4i Landry ML, Burns NZ. Acc. Chem. Res. 2018; 51: 1260

5a Xu H, Tang H, Feng H, Li Y. Tetrahedron Lett. 2014; 55: 7118
5b Xu H, Tang H, Feng H, Li Y. J. Org. Chem. 2014; 79: 10110

6 Surendra K, Qiu W, Corey EJ. J. Am. Chem. Soc. 2011; 133: 9724

7a Barrett TN, Barrett AG. M. J. Am. Chem. Soc. 2014; 136: 17013
7b Ma T.-K, Elliott DC, Reid S, White AJ. P, Parsons PJ, Barrett AG. M. J. Org. Chem. 2018; 83: 13276

8 Rosen BR, Werner EW, O’Brien AG, Baran PS. J. Am. Chem. Soc. 2014; 136: 5571
9 Suzuki K, Yamakoshi H, Nakamura S. Chem. Eur. J. 2015; 21: 17605
10 Rajendar G, Corey EJ. J. Am. Chem. Soc. 2015; 137: 5837
11 Camelio AM, Johnson TC, Siegel D. J. Am. Chem. Soc. 2015; 137: 11864

12a Speck K, Wildermuth R, Magauer T. Angew. Chem. Int. Ed. 2016; 55: 14131
12b Speck K, Magauer T. Chem. Eur. J. 2017; 23: 1157

13 Chan C.-K, Chen Y.-H, Chang M.-Y. Tetrahedron 2016; 72: 5121
14 Minassi A, Pollastro F, Chianese G, Caprioglio D, Taglialatela-Scafati O, Appendino G. Angew. Chem. Int. Ed. 2017; 56: 7935
15 Graham M, Baker RW, McErlean CS. P. Eur. J. Org. Chem. 2017; 908
16 Saito Y, Goto M, Nakagawa-Goto K. Org. Lett. 2018; 20: 628
17 Zhang F.-Z, Tian Y, Li G.-X, Qu J. J. Org. Chem. 2015; 80: 1107
18 Tian Y, Xu X, Zhang L, Qu J. Org. Lett. 2016; 18: 268

19a Ishihara K, Nakamura S, Yamamoto H. J. Am. Chem. Soc. 1999; 121: 4906
19b Nakamura S, Ishihara K, Yamamoto H. J. Am. Chem. Soc. 2000; 122: 8131
19c Ishihara K, Ishibashi H, Yamamoto H. J. Am. Chem. Soc. 2001; 123: 1505
19d Ishihara K, Ishibashi H, Yamamoto H. J. Am. Chem. Soc. 2002; 124: 3647
19e Ishibashi H, Ishihara K, Yamamoto H. J. Am. Chem. Soc. 2004; 126: 11122
19f Surendra K, Corey EJ. J. Am. Chem. Soc. 2012; 134: 11992
19g Surendra K, Rajendar G, Corey EJ. J. Am. Chem. Soc. 2014; 136: 642

20 Lin S.-C, Chein R.-J. J. Org. Chem. 2017; 82: 1575
21 Elkin M, Szewczyk SM, Scruse AC, Newhouse TR. J. Am. Chem. Soc. 2017; 139: 1790
22 Fan L, Han C, Li X, Yao J, Wang Z, Yao C, Chen W, Wang T, Zhao J. Angew. Chem. Int. Ed. 2018; 57: 2115
23 Alonso P, Fontaneda R, Pardo P, Fañanás FJ, Rodríguez F. Org. Lett. 2018; 20: 1659
24 Peng X.-R, Lu S.-Y, Shao L.-D, Zhou L, Qiu M.-H. J. Org. Chem. 2018; 83: 5516

25a Snyder SA, Treitler DS. Angew. Chem. Int. Ed. 2009; 48: 7899
25b Snyder SA, Treitler DS, Brucks AP. J. Am. Chem. Soc. 2010; 132: 14303

26 Shen M, Kretschmer M, Brill ZG, Snyder SA. Org. Lett. 2016; 18: 5018
27 Samanta RC, Yamamoto H. J. Am. Chem. Soc. 2017; 139: 1460
28 Alonso P, Pardo P, Fontaneda R, Fañanás FJ, Rodríguez F. Chem. Eur. J. 2017; 23: 13158
29 Ascheberg C, Bock J, Buß F, Mück-Lichtenfeld C, Daniliuc CG, Bergander K, Dielmann F, Hennecke U. Chem. Eur. J. 2017; 23: 11578
30 Arnold AM, Pöthig A, Drees M, Gulder T. J. Am. Chem. Soc. 2018; 140: 4344
31 Schevenels FT, Shen M, Snyder SA. Org. Lett. 2017; 19: 2
32 Cole C, Chi H, DeBacker K, Snyder S. Synthesis 2018; 50: A-H
33 Tao Z, Robb KA, Zhao K, Denmark SE. J. Am. Chem. Soc. 2018; 140: 3569
34 Geier MJ, Gagné MR. J. Am. Chem. Soc. 2014; 136: 3032
35 McCulley CH, Geier MJ, Hudson BM, Gagné MR, Tantillo DJ. J. Am. Chem. Soc. 2017; 139: 11158

36a Toullec PY, Blarre T, Michelet V. Org. Lett. 2009; 11: 2888
36b Sethofer SG, Mayer T, Toste FD. J. Am. Chem. Soc. 2010; 132: 8276
36c Pradal A, Chen Q, Faudot dit Bel P, Toullec P, Michelet V. Synlett 2012; 2012: 74

37 Rong Z, Echavarren AM. Org. Biomol. Chem. 2017; 15: 2163
38 Lai Y, Zhang N, Zhang Y, Chen J.-H, Yang Z. Org. Lett. 2018; 20: 4298
39 Schafroth MA, Sarlah D, Krautwald S, Carreira EM. J. Am. Chem. Soc. 2012; 134: 20276
40 Zhou S, Guo R, Yang P, Li A. J. Am. Chem. Soc. 2018; 140: 9025

41a Breslow R, Barrett E, Mohacsi E. Tetrahedron Lett. 1962; 3: 1207
41b Breslow R, Olin SS, Groves JT. Tetrahedron Lett. 1968; 9: 1837

42 Curran DP, Porter NA, Giese B. Stereochemistry of Radical Reactions . VCH; Weinheim: 1995
43 Rosales A, Muñoz-Bascón J, Roldan-Molina E, Rivas-Bascón N, Padial NM, Rodríguez-Maecker R, Rodríguez-García I, Oltra JE. J. Org. Chem. 2015; 80: 1866
44 Fuse S, Ikebe A, Oosumi K, Karasawa T, Matsumura K, Izumikawa M, Johmoto K, Uekusa H, Shin-ya K, Doi T, Takahashi T. Chem.–Eur. J. 2015; 21: 9454
45 Göhl M, Seifert K. Eur. J. Org. Chem. 2015; 6249
46 Trotta AH. Org. Lett. 2015; 17: 3358
47 Sun Y, Meng Z, Chen P, Zhang D, Baunach M, Hertweck C, Li A. Org. Chem. Front. 2016; 3: 368
48 Furuta M, Hanaya K, Sugai T, Shoji M. Tetrahedron 2017; 73: 2316
49 Deng H, Cao W, Liu R, Zhang Y, Liu B. Angew. Chem. Int. Ed. 2017; 56: 5849
50 Cao W, Deng H, Sun Y, Liu B, Qin S. Chem. Eur. J. 2018; 24: 9120
51 Merchant RR, Oberg KM, Lin Y, Novak AJ. E, Felding J, Baran PS. J. Am. Chem. Soc. 2018; 140: 7462

52a Hoffmann U, Gao Y, Pandey B, Klinge S, Warzecha K.-D, Krueger C, Roth HD, Demuth M. J. Am. Chem. Soc. 1993; 115: 10358
52b Heinemann C, Demuth M. J. Am. Chem. Soc. 1997; 119: 1129
52c Heinemann C, Demuth M. J. Am. Chem. Soc. 1999; 121: 4894
52d Goeller F, Heinemann C, Demuth M. Synthesis 2001; 1114
52e Rosales V, Zambrano J, Demuth M. Eur. J. Org. Chem. 2004; 1798
52f Ozser ME, Icil H, Makhynya Y, Demuth M. Eur. J. Org. Chem. 2004; 3686

53 Yang Z, Li H, Zhang L, Zhang M.-T, Cheng J.-P, Luo S. Chem. Eur. J. 2015; 21: 14723
54 Yang Z, Li S, Luo S. Acta Chim. Sin. 2017; 75: 351
55 Trotta AH. J. Org. Chem. 2017; 82: 13500