Recent Synthetic Strategies to Access Seven-Membered Carbocycles in Natural Product Synthesis

Thanh Vinh Nguyen; Jan Marc Hartmann; Dieter Enders

doi:10.1055/s-0032-1318152

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(7): 845-873
DOI: 10.1055/s-0032-1318152

review

Recent Synthetic Strategies to Access Seven-Membered Carbocycles in Natural Product Synthesis

Authors

Thanh Vinh Nguyen

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 eMail: enders@rwth.aachen.de
Jan Marc Hartmann

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 eMail: enders@rwth.aachen.de
Dieter Enders*

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 eMail: enders@rwth.aachen.de

Abstract

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Abstract

This methodology-oriented review covers the synthetic strategies to construct seven-membered carbocycles in naturally occurring compounds over the last ten years. It offers an insight into the common synthetic targets and approaches and provides useful information for further developments within this area of natural product synthesis as well as synthetic methodology in general.

1 Introduction

2 Cyclization Reactions

3 Cycloaddition Reactions

3.1 [5+2] Cycloaddition

3.2 [4+3] Cycloaddition

3.3 Diels–Alder Reactions

3.4 [2+2+2] Cycloaddition

4 Ring-Closing Metathesis

4.1 Ene–Ene Metathesis

4.2 Ene–Yne Metathesis

5 Ring-Expansion and Ring-Contraction Reactions

5.1 Ring-Expansion Reactions

5.2 Ring-Contraction Reactions

6 Fragmentation and Isomerization Reactions

7 Other Frequently Targeted Natural Products

8 Conclusion

Key words

seven-membered carbocycles - natural products - total synthesis - synthetic strategy - medium-sized carbocycles

Volltext

Referenzen

References
1 Battiste MA, Pelphrey PM, Wright DL. Chem. Eur. J. 2006; 12: 3438
2 Pellissier H. Adv. Synth. Catal. 2011; 353: 189
3 Narayan AR. H, Simmons EM, Sarpong R. Eur. J. Org. Chem. 2010; 3553
4 Pouwer RH, Richard J.-A, Tseng C.-C, Chen DY. K. Chem. Asian J. 2012; 7: 22
5 Inoue M, Carson MW, Frontier AJ, Danishefsky SJ. J. Am. Chem. Soc. 2001; 123: 1878

6a Hughes CC, Trauner D. Angew. Chem. Int. Ed. 2002; 41: 1569
6b Hughes CC, Trauner D. Tetrahedron 2004; 60: 9675

7 Ovaska TV, Sullivan JA, Ovaska SI, Winegrad JB, Fair JD. Org. Lett. 2009; 11: 2715
8 Taj RA, Green JR. J. Org. Chem. 2010; 75: 8258
9 Mandal M, Yun H, Dudley GB, Lin S, Tan DS, Danishefsky SJ. J. Org. Chem. 2005; 70: 10619
10 Justicia J, Oller-Lopez JL, Campana AG, Oltra JE, Cuerva JM, Bunuel E, Cardenas DJ. J. Am. Chem. Soc. 2005; 127: 14911
11 Miller AK, Hughes CC, Kennedy-Smith JJ, Gradl SN, Trauner D. J. Am. Chem. Soc. 2006; 128: 17057
12 Moeller KD. Tetrahedron 2000; 56: 9527
13 Sperry JB, Wright DL. Chem. Soc. Rev. 2006; 35: 605
14 Bisai A, West SP, Sarpong R. J. Am. Chem. Soc. 2008; 130: 7222
15 Mukaiyama T. Org. React. (N.Y.) 1982; 28: 203
16 Nicolaou KC, Sun Y.-P, Peng X.-S, Polet D, Chen DY. K. Angew. Chem. Int. Ed. 2008; 47: 7310
17 Shenvi RA, Guerrero CA, Shi J, Li C.-C, Baran PS. J. Am. Chem. Soc. 2008; 130: 7241
18 Nicolaou KC, Peng X.-S, Sun Y.-P, Polet D, Zou B, Lim CS, Chen DY. K. J. Am. Chem. Soc. 2009; 131: 10587
19 Li X, Keon AE, Sullivan JA, Ovaska TV. Org. Lett. 2008; 10: 3287
20 Mehta G, Likhite NS. Tetrahedron Lett. 2008; 49: 7113
21 Mehta G, Likhite NS, Ananda Kumar CS. Tetrahedron Lett. 2009; 50: 5260
22 Marion F, Williams DE, Patrick BO, Hollander I, Mallon R, Kim SC, Roll DM, Feldberg L, Van Soest R, Andersen RJ. Org. Lett. 2006; 8: 321
23 Masters K.-S, Flynn BL. Org. Biomol. Chem. 2010; 8: 1290
24 Kerr DJ, Willis AC, Flynn BL. Org. Lett. 2004; 6: 457
25 Nicolaou KC, Ding H, Richard J.-A, Chen DY. K. J. Am. Chem. Soc. 2010; 132: 3815
26 Dong M, Cong B, Yu S.-H, Sauriol F, Huo C.-H, Shi Q.-W, Gu Y.-C, Zamir LO, Kiyota H. Org. Lett. 2008; 10: 701
27 Reiter M, Torssell S, Lee S, MacMillan DW. C. Chem. Sci. 2010; 1: 37
28 Kanoh N, Sakanishi K, Iimori E, Nishimura K, Iwabuchi Y. Org. Lett. 2011; 13: 2864
29 Tang CH, Li ZY, Wang YY, Xu JY, Kong LY, Yao HQ, Wu XM. Tetrahedron Lett. 2011; 52: 3275

30a Dohi T, Ito M, Yamaoka N, Morimoto K, Fujioka H, Kita Y. Tetrahedron 2009; 65: 10797
30b Kita Y, Tohma H, Hatanaka K, Takada T, Fujita S, Mitoh S, Sakurai H, Oka S. J. Am. Chem. Soc. 1994; 116: 3684
30c Kita Y, Tohma H, Inagaki M, Hatanaka K, Yakura T. Tetrahedron Lett. 1991; 32: 4321

31a Oliver SF, Högenauer K, Simic O, Antonello A, Smith MD, Ley SV. Angew. Chem. Int. Ed. 2003; 42: 5996
31b Andrews SP, Ball M, Wierschem F, Cleator E, Oliver S, Högenauer K, Simic O, Antonello A, Hünger U, Smith MD, Ley SV. Chem. Eur. J. 2007; 13: 5688

32 Yang HS, Gao YZ, Qiao XX, Xie LG, Xu XH. Org. Lett. 2011; 13: 3670
33 Adachi M, Yamada H, Isobe M, Nishikawa T. Org. Lett. 2011; 13: 6532
34 Nakamura S, Sugano Y, Kikuchi F, Hashimoto S. Angew. Chem. Int. Ed. 2006; 45: 6532
35 Snider BB, Grabowski JF. Tetrahedron Lett. 2005; 46: 823
36 Li Y, Nawrat CC, Pattenden G, Winne JM. Org. Biomol. Chem. 2009; 7: 639
37 Weiss ME, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 11501
38 Wender PA, Zhang L. Org. Lett. 2000; 2: 2323
39 Trost BM, Hu Y, Horne DB. J. Am. Chem. Soc. 2007; 129: 11781
40 Trost BM, Waser J, Meyer A. J. Am. Chem. Soc. 2008; 130: 16424

41a Hendrickson JB, Farina JS. J. Org. Chem. 1980; 45: 3359
41b Hendrickson JB, Farina JS. J. Org. Chem. 1980; 45: 3361

42a Sammes PG, Street LJ. J. Chem. Soc., Chem. Commun. 1982; 1056
42b Sammes PG, Street LJ. J. Chem. Soc., Perkin Trans. 1 1983; 1261
42c Sammes PG, Street LJ. J. Chem. Soc., Perkin Trans. 1 1983; 2729
42d Sammes PG, Street LJ. J. Chem. Res., Synop. 1984; 196
42e Sammes PG. Gazz. Chim. Ital. 1986; 116: 109

43 Marshall KA, Mapp AK, Heathcock CH. J. Org. Chem. 1996; 61: 9135
44 Ohmori N. J. Chem. Soc., Perkin Trans. 1 2002; 755
45 Snider BB, Grabowski JF. Tetrahedron 2006; 62: 5171

46a Snider BB, Wu X, Nakamura S, Hashimoto S. Org. Lett. 2007; 9: 873
46b Sugano Y, Kikuchi F, Toita A, Nakamura S, Hashimoto S. Chem. Eur. J. 2012; 18: 9682

47 Tang B, Bray CD, Pattenden G. Org. Biomol. Chem. 2009; 7: 4448
48 Roethle PA, Hernandez PT, Trauner D. Org. Lett. 2006; 8: 5901
49 Lee K, Cha JK. J. Am. Chem. Soc. 2001; 123: 5590
50 Wender PA, Rice KD, Schnute ME. J. Am. Chem. Soc. 1997; 119: 7897
51 Lee JC, Cha JK. J. Am. Chem. Soc. 2001; 123: 3243
52 Davies HM. L, Denton JR. Chem. Soc. Rev. 2009; 38: 3061
53 Reddy RP, Davies HM. L. J. Am. Chem. Soc. 2007; 129: 10312
54 Olson JP, Davies HM. L. Org. Lett. 2008; 10: 573
55 Schwartz BD, Denton JR, Lian Y, Davies HM. L, Williams CM. J. Am. Chem. Soc. 2009; 131: 8329
56 Schwartz BD, Denton JR, Davies HM. L, Williams CM. Aust. J. Chem. 2009; 62: 980
57 Lian YJ, Miller LC, Born S, Sarpong R, Davies HM. L. J. Am. Chem. Soc. 2010; 132: 12422
58 Garayalde D, Kruger K, Nevado C. Angew. Chem. Int. Ed. 2011; 50: 911
59 Nilson MG, Funk RL. J. Am. Chem. Soc. 2011; 133: 12451
60 Liu LZ, Han JC, Yue GZ, Li CC, Yang Z. J. Am. Chem. Soc. 2010; 132: 13608
61 Peixoto PA, Severin R, Tseng C.-C, Chen DY. K. Angew. Chem. 2011; 123: 3069
62 Michelet V, Toullec PY, Genêt J.-P. Angew. Chem. Int. Ed. 2008; 47: 4268
63 Magauer T, Mulzer J, Tiefenbacher K. Org. Lett. 2009; 11: 5306
64 Peixoto PA, Richard J.-A, Severin R, Chen DY. K. Org. Lett. 2011; 13: 5724
65 Jimenez-Nunez E, Molawi K, Echavarren AM. Chem. Commun. 2009; 7327
66 Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4490
67 Shi B, Hawryluk NA, Snider BB. J. Org. Chem. 2003; 68: 1030
68 Lin S, Dudley GB, Tan DS, Danishefsky SJ. Angew. Chem. Int. Ed. 2002; 41: 2188
69 Nakashima K, Inoue K, Sono M, Tori M. J. Org. Chem. 2002; 67: 6034
70 Nakashima K, Fujisaki N, Inoue K, Minami A, Nagaya C, Sono M, Tori M. Bull. Chem. Soc. Jpn. 2006; 79: 1955
71 Weatherhead GS, Cortez GA, Schrock RR, Hoveyda AH. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5805
72 Fan W, White JB. J. Org. Chem. 1993; 58: 3557
73 Elford TG, Hall DG. J. Am. Chem. Soc. 2010; 132: 1488
74 Monrad RN, Pipper CB, Madsen R. Eur. J. Org. Chem. 2009; 3387
75 Mehta G, Pallavi K, Umarye JD. Chem. Commun. 2005; 4456

76a Michalak K, Michalak M, Wicha J. J. Org. Chem. 2010; 75: 8337
76b Michalak K, Michalak M, Wicha J. Tetrahedron Lett. 2010; 51: 4344

77 Flyer AN, Si C, Myers AG. Nat. Chem. 2010; 2: 886

78a Lee HM, Nieto-Oberhuber C, Shair MD. J. Am. Chem. Soc. 2008; 130: 16864
78b Shoji M. J. Synth. Org. Chem. Jpn. 2009; 67: 949

79 Radtke L, Willot M, Sun H, Ziegler S, Sauerland S, Strohmann C, Fröhlich R, Habenberger P, Waldmann H, Christmann M. Angew. Chem. Int. Ed. 2011; 50: 3998
80 Willot M, Radtke L, Koenning D, Fröhlich R, Gessner VH, Strohmann C, Christmann M. Angew. Chem. Int. Ed. 2009; 48: 9105
81 Liu G, Romo D. Angew. Chem. Int. Ed. 2011; 50: 7537
82 Ohyoshi T, Funakubo S, Miyazawa Y, Niida K, Hayakawa I, Kigoshi H. Angew. Chem. Int. Ed. 2012; 51: 4972
83 Boyer F.-D, Hanna I, Ricard L. Org. Lett. 2004; 6: 1817
84 Tan DS, Dudley GB, Danishefsky SJ. Angew. Chem. Int. Ed. 2002; 41: 2185
85 Kummer DA, Brenneman JB, Martin SF. Tetrahedron 2006; 62: 11437

86a For a review on the previous total syntheses of colchicines, see: Graening T, Schmalz H.-G. Angew. Chem. Int. Ed. 2004; 43: 3230
86b Boyer FD, Hanna I. Org. Lett. 2007; 9: 2293

87a Nakamura T. Chem. Pharm. Bull. 1962; 10: 299
87b Nakamura T, Murase Y, Endo Y, Hayashi R. Chem. Pharm. Bull. 1962; 10: 281

88 Boyer FD, Hanna I. Eur. J. Org. Chem. 2008; 4938
89 George JH, Baldwin JE, Adlington RM. Org. Lett. 2010; 12: 2394
90 Alvarez-Manzaneda E, Chahboun R, Alvarez E, Cano MJ, Haidour A, Alvarez-Manzaneda R. Org. Lett. 2010; 12: 4450

91a Elamparuthi E, Fellay C, Neuburger M, Gademann K. Angew. Chem. Int. Ed. 2012; 51: 4071
91b Watanabe H, Takano M, Nakada M. J. Synth. Org. Chem. Jpn. 2008; 66: 1116

92 Feldman KS, Ngernmeesri P. Org. Lett. 2011; 13: 5704
93 Feldman KS, Cutarelli TD, Di Florio R. J. Org. Chem. 2002; 67: 8528
94 Hong S.-K, Kim H, Seo Y, Lee SH, Cha JK, Kim YG. Org. Lett. 2010; 12: 3954
95 Shipe WD, Sorensen EJ. J. Am. Chem. Soc. 2006; 128: 7025
96 Simmons EM, Hardin-Narayan AR, Guo X, Sarpong R. Tetrahedron 2010; 66: 4696
97 Chatani N, Inoue H, Kotsuma T, Murai S. J. Am. Chem. Soc. 2002; 124: 10294
98 Yamashita S, Kitajima K, Iso K, Hirama M. Tetrahedron Lett. 2009; 50: 3277
99 Gampe CM, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 2962
100 Day JJ, McFadden RM, Virgil SC, Kolding H, Alleva JL, Stoltz BM. Angew. Chem. Int. Ed. 2011; 50: 6814
101 Schnermann MJ, Overmann LE. Angew. Chem. Int. Ed. 2012; 51: 9576
102 Kuwajima I, Tanino K. Chem. Rev. 2005; 105: 4661
103 Huters AD, Styduhar ED, Garg NK. Angew. Chem. Int. Ed. 2012; 51: 3758