Synthesis of Polycyclic Natural Products through Skeletal Rearrangement

Satoshi Yokoshima

doi:10.1055/s-0040-1707904

Synlett, Table of Contents

Synlett 2020; 31(20): 1967-1975
DOI: 10.1055/s-0040-1707904

account

Synthesis of Polycyclic Natural Products through Skeletal Rearrangement

Authors

Satoshi Yokoshima ∗

Abstract

All articles of this category

Abstract

Construction of rings through reliable reactions followed by changes in the ring size or the connectivity through skeletal rearrangement provides molecules with a wide range of skeletons. In this account, our syntheses of polycyclic natural products through skeletal rearrangement are discussed.

1 Introduction

2 Synthesis through Changes in the Ring Size

3 Synthesis by Biomimetic Strategies

4 Synthesis through Metathesis

5 Synthesis through Temporary Formation of a Ring

6 Conclusion

Key words

alkaloids - cycloaddition - natural products - rearrangement - total synthesis

Full Text

References

References

1a Newman DJ, Cragg GM. J. Nat. Prod. 2016; 79: 629
1b Newman DJ, Cragg GM. J. Nat. Prod. 2020; 83: 770
1c Gerry CJ, Schreiber SL. Nat. Rev. Drug Discovery 2018; 17: 333
1d Davison EK, Brimble MA. Curr. Opin. Chem. Biol. 2019; 52: 1

2a Lachance H, Wetzel S, Kumar K, Waldmann H. J. Med. Chem. 2012; 55: 5989
2b Kaiser M, Wetzel S, Kumar K, Waldmann H. Cell. Mol. Life Sci. 2008; 65: 1186

3a Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
3b Lovering F. MedChemComm 2013; 4: 515

4a Yokoshima S. Chem. Pharm. Bull. 2013; 61: 251
4b Yokoshima S. Yuki Gosei Kagaku Kyokaishi 2017; 75: 1035

For selected reviews on Diels–Alder reaction, see:

5a Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
5b Takao K.-i, Munakata R, Tadano K.-i. Chem. Rev. 2005; 105: 4779
5c Foster RA. A, Willis MC. Chem. Soc. Rev. 2013; 42: 63
5d Jiang X, Wang R. Chem. Rev. 2013; 113: 5515
5e Xie M, Lin L, Feng X. Chem. Rec. 2017; 17: 1184
5f Yang B, Gao S. Chem. Soc. Rev. 2018; 47: 7926

6 You L, Liang X.-T, Xu L.-M, Wang Y.-F, Zhang J.-J, Su Q, Li Y.-H, Zhang B, Yang S.-L, Chen J.-H, Yang Z. J. Am. Chem. Soc. 2015; 137: 10120
7 Kobayashi J, Hirasawa Y, Yoshida N, Morita H. J. Org. Chem. 2001; 66: 5901

8a Nishimura T, Unni AK, Yokoshima S, Fukuyama T. J. Am. Chem. Soc. 2011; 133: 418; corrigendum: J. Am. Chem. Soc. 2014, 136, 5818
8b Nishimura T, Unni AK, Yokoshima S, Fukuyama T. J. Am. Chem. Soc. 2013; 135: 3243 ; corrigendum: J. Am. Chem. Soc. 2013, 136, 5817

For other syntheses of lyconadin A, see:

9a Beshore DC, Smith AB. III. J. Am. Chem. Soc. 2007; 129: 4148
9b Bisai A, West SP, Sarpong R. J. Am. Chem. Soc. 2008; 130: 7222
9c Lee AS, Liau BB, Shair MD. J. Am. Chem. Soc. 2014; 136: 13442
9d Yang Y, Haskins CW, Zhang W, Low PL, Dai M. Angew. Chem. Int. Ed. 2014; 53: 3922
9e Yang Y, Dai M. Synlett 2014; 25: 2093
9f Zhang J, Yan Y, Hu R, Li T, Bai W.-J, Yang Y. Angew. Chem. Int. Ed. 2020; 59: 2860

10a Nilsson BL, Overman LE, Read De Alaniz J, Rohde JM. J. Am. Chem. Soc. 2008; 130: 11297
10b Altman RA, Nilsson BL, Overman LE, Read De Alaniz J, Rohde JM, Taupin V. J. Org. Chem. 2010; 75: 7519

11 Fujii M, Nishimura T, Koshiba T, Yokoshima S, Fukuyama T. Org. Lett. 2013; 15: 232 ; corrigendum: Org. Lett. 2014, 16, 1272
12 Tan C.-H, Ma X.-Q, Chen G.-F, Zhu D.-Y. Helv. Chim. Acta 2002; 85: 1058
13 Tanimura S, Yokoshima S, Fukuyama T. Org. Lett. 2017; 19: 3684

For other syntheses of huperzine Q, see:

14a Nakayama A, Kogure N, Kitajima M, Takayama H. Angew. Chem. Int. Ed. 2011; 50: 8025
14b Hong B, Li H, Wu J, Zhang J, Lei X. Angew. Chem. Int. Ed. 2015; 54: 1011
14c Zeng C, Zhao J, Zhao G. Tetrahedron 2015; 71: 64
14d Hong B, Hu D, Wu J, Zhang J, Li H, Pan Y, Lei X. Chem. Asian J. 2017; 12: 1557

15 House HO, Wasson RL. J. Am. Chem. Soc. 1957; 79: 1488

For selected reviews on biomimetic synthesis of natural products, see:

16a Bulger PG, Bagal SK, Marquez R. Nat. Prod. Rep. 2008; 25: 254
16b Kim J, Movassaghi M. Chem. Soc. Rev. 2009; 38: 3035
16c Poupon E. Planta Med. 2012; 78: IL44
16d Jürjens G, Kirschning A, Candito DA. Nat. Prod. Rep. 2015; 32: 723
16e Takayama H. Chem. Pharm. Bull. 2020; 68: 103

17 Tan C.-H, Chen G.-F, Ma X.-Q, Jiang S.-H, Zhu D.-Y. J. Nat. Prod. 2002; 65: 1021
18 Kumazaki H, Nakajima R, Bessho Y, Yokoshima S, Fukuyama T. Synlett 2015; 26: 2131
19 Nomura T, Yokoshima S, Fukuyama T. Org. Lett. 2018; 20: 119
20 Donald JR, Unsworth WP. Chem. Eur. J. 2017; 23: 8780

21a Takayama H, Katakawa K, Kitajima M, Yamaguchi K, Aimi N. Tetrahedron Lett. 2002; 43: 8307
21b Nakayama A, Kogure N, Kitajima M, Takayama H. Org. Lett. 2009; 11: 5554

22 Churykau DH, Zinovich VG, Kulinkovich OG. Synlett 2004; 1949
23 González AG, De La Fuente G, Reina M, Zabel V, Watson WH. Tetrahedron Lett. 1980; 21: 1155

24a Wiesner K, Tsai TY. R, Huber K, Bolton SE, Vlahov R. J. Am. Chem. Soc. 1974; 96: 4990
24b Wiesner K. Tetrahedron 1985; 41: 485
24c Marth CJ, Gallego GM, Lee JC, Lebold TP, Kulyk S, Kou KG. M, Qin J, Lilien R, Sarpong R. Nature 2015; 528: 493
24d Kou KG. M, Kulyk S, Marth CJ, Lee JC, Doering NA, Li BX, Gallego GM, Lebold TP, Sarpong R. J. Am. Chem. Soc. 2017; 139: 13882
24e Kamakura D, Todoroki H, Urabe D, Hagiwara K, Inoue M. Angew. Chem. Int. Ed. 2020; 59: 479

25 Gin and co-workers accomplished a synthesis of an aconitine-type norditerpenoid alkaloid, neofinaconitine, without using the Wagner–Meerwein rearrangement; see: Shi Y, Wilmot JT, Nordstrøm LU, Tan DS, Gin DY. J. Am. Chem. Soc. 2013; 135: 14313

26a Nishiyama Y, Yokoshima S, Fukuyama T. Org. Lett. 2016; 18: 2359
26b Nishiyama Y, Yokoshima S, Fukuyama T. Org. Lett. 2017; 19: 5833

27 Nishiyama Y, Han-Ya Y, Yokoshima S, Fukuyama T. J. Am. Chem. Soc. 2014; 136: 6598

For reviews on the oxidative dearomatization/Diels–Alder reaction sequence, see:

28a Liao C.-C, Peddinti RK. Acc. Chem. Res. 2002; 35: 856
28b Magdziak D, Meek SJ, Pettus TR. R. Chem. Rev. 2004; 104: 1383
28c Pouységu L, Deffieux D, Quideau S. Tetrahedron 2010; 66: 2235
28d Roche SP, Porco JA. Jr. Angew. Chem. Int. Ed. 2011; 50: 4068
28e Liu X.-Y, Qin Y. Nat. Prod. Rep. 2017; 34: 1044

For selected reviews on ring-closing metathesis, see:

29a Kotha S, Meshram M, Khedkar P, Banerjee S, Deodhar D. Beilstein J. Org. Chem. 2015; 11: 1833
29b Han J.-C, Li C.-C. Chem. Rec. 2017; 17: 499
29c Lecourt C, Dhambri S, Allievi L, Sanogo Y, Zeghbib N, Ben Othman R, Lannou MI, Sorin G, Ardisson J. Nat. Prod. Rep. 2018; 35: 105
29d Kotha S, Meshram M, Dommaraju Y. Chem. Rec. 2018; 18: 1613
29e Cheng-Sánchez I, Sarabia F. Synthesis 2018; 50: 3749

30a Miura Y, Hayashi N, Yokoshima S, Fukuyama T. J. Am. Chem. Soc. 2012; 134: 11995
30b Hayashi N, Miura Y, Yokoshima S, Fukuyama T. Chem. Pharm. Bull. 2019; 67: 64

For other syntheses of isoschizogamine, see:

31a Hubbs JL, Heathcock CH. Org. Lett. 1999; 1: 1315
31b Wang X, Xia D, Tan L, Chen H, Huang H, Song H, Qin Y. Chem. Eur. J. 2015; 21: 14602
31c Takada A, Fujiwara H, Sugimoto K, Ueda H, Tokuyama H. Chem. Eur. J. 2015; 21: 16400
31d Xu Z, Bao X, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2015; 54: 14937

32a Renner U. Lloydia 1964; 27: 406
32b Hájíček J, Taimr J, Buděšínský M. Tetrahedron Lett. 1998; 39: 505

33 Kleinfelter DC, Gerteisen TJ. J. Org. Chem. 1971; 36: 3255
34 Stewart IC, Ung T, Pletnev AA, Berlin JM, Grubbs RH, Schrodi Y. Org. Lett. 2007; 9: 1589
35 Itooka R, Iguchi Y, Miyaura N. J. Org. Chem. 2003; 68: 6000
36 Murakami K, Toma T, Fukuyama T, Yokoshima S. Angew. Chem. Int. Ed. 2020; 59: 6253

For our other results on skeletal rearrangements, see:

37a Yamada R, Fukuyama T, Yokoshima S. Org. Lett. 2018; 20: 4504
37b Watanabe S, Ishikawa M, Nomura T, Fukuyama T, Yokoshima S. Synlett 2018; 29: 2377