Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones

doi:10.6023/cjoc202109025

Abstract

2-Pyrone is a type of heterocycles with a conjugated diene motif. It can react as a privileged diene in Diels-Alder reactions. In the past several decades, 2-pyrone-based Diels-Alder reactions have been widely used in the total synthesis of complex natural products. Therefore, the catalytic asymmetric Diels-Alder reactions of 2-pyrones have attracted increasing attention from the synthetic community in recent years. The research progress of catalytic asymmetric normal-electron-demand Diels-Alder reactions and inverse-electron-demand Diels-Alder reactions, and their applications in total synthesis of natural products are summarized.

Key words: 2-pyrone, Diels-Alder reactions, asymmetric catalysis, total synthesis of natural products

Cite this article

Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.

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Fig. & Tab. 22

Scheme 1. The first example of Diels-Alder reaction of 2-pyrone

Scheme 2. Diels-Alder reaction of 2-pyrones

Scheme 3. Normal-electron-demand Diels-Alder (NEDDA) reaction and inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones

Scheme 4. Aapplications of 2-pyrone-based Diels-Alder reaction in natural product synthesis

Scheme 5. Asymmetric Diels-Alder reactions of 2-pyrones with maleimide

Scheme 6. Asymmetric Diels-Alder reactions of 2-pyrones with benzoylacrylic esters

Scheme 7. Asymmetric Diels-Alder reactions of 2-pyrones with enones

Scheme 8. Asymmetric Diels-Alder reactions of 2-pyrone with N-phenyl-maleimide

Scheme 9. Asymmetric Diels-Alder reactions of 2-pyrones with nitroalkenes

Scheme 10. Asymmetric Diels-Alder reactions of 2-pyrones with cyclopentendiones

Scheme 11. Asymmetric total synthesis of (+)-iso-A82775C

Scheme 12. Aymmetric total synthesis of (+)-calvicularin

Scheme 13. Synthesis of common intermediate 50

Scheme 14. Total synthesis of crotophorbolone, langduin A, prostratin, resiniferatoxin and tinyatoxin

Scheme 15. First examples of IEDDA reactions of 2-pyrones

Scheme 16. Asymmetric total synthesis of calcitriol

Scheme 17. Cu-catalyzed asymmetric IEDDA reaction of 2-pyrones and vinylselenides

Scheme 18. Asymmetric synthesis of arene cis-dihydrodiols

Scheme 19. Asymmetric synthesis of cis-decalins

Scheme 20. Asymmetric synthesis of axially chiral biaryls

Scheme 21. Asymmetric Diels-Alder reactions of 2-pyrones with cyclic 2,5-dienones

Scheme 22. Asymmetric Diels-Alder reactions of 2-pyrones with α,β-unsaturated aldehydes

References 46

[1]	Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1928, 460, 98. doi: 10.1002/(ISSN)1099-0690
[2]	(a) Hoffmann, R.; Woodward, R. B. Acc. Chem. Res. 1968, 1, 17. doi: 10.1021/ar50001a003
	(b) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. doi: 10.1002/(ISSN)1521-3773
	(c) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T. M.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668. doi: 10.1002/(ISSN)1521-3773
[3]	Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1931, 490, 257. doi: 10.1002/(ISSN)1099-0690
[4]	(a) Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111. doi: 10.1016/S0040-4020(01)85607-6
	(b) Cai, Q. Chin. J. Chem. 2019, 37, 946. doi: 10.1002/cjoc.v37.9
	(c) Huang, G.; Kouklovsky, C.; de la Torre, A. Chem.-Eur. J. 2021, 27, 4760. doi: 10.1002/chem.v27.15
[5]	Watt, D. S.; Corey, E. J. Tetrahedron Lett. 1972, 13, 4651. doi: 10.1016/S0040-4039(01)94389-8
[6]	(a) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118.
	(b) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Nature 1997, 367, 630. doi: 10.1038/367630a0
[7]	Baran, P. S.; Burns, N. Z. J. Am. Chem. Soc. 2006, 128, 3908. pmid: 16551088
[8]	Shim, I.-J.; Choi, E.-S.; Cho, C.-G. Angew. Chem., Int. Ed. 2007, 46, 2303. doi: 10.1002/(ISSN)1521-3773
[9]	Smith, M. W.; Synder, S. A. A. J. Am. Chem. Soc. 2013, 135, 12964. doi: 10.1021/ja406546k
[10]	Yu, X.; Xiao, L.; Wang, Z.; Luo, T. J. Am. Chem. Soc. 2019, 141, 3440. doi: 10.1021/jacs.9b00621
[11]	Okamura, H.; Nakamura, Y.; Iwagawa, T.; Nakatani, M. Chem. Lett. 1996, 193.
[12]	Shen, J.; Tan, C.-H. Org. Biomol. Chem. 2008, 6, 3229. doi: 10.1039/b809505c
[13]	Wang, Y.; Li, H.; Wang, Y.-Q.; Liu, Y.; Foxman, B. M.; Deng, L. J. Am. Chem. Soc. 2007, 129, 6364. pmid: 17469829
[14]	Singh, R. P.; Bartelson, K.; Wang, Y.; Su, H.; Lu, X.; Deng, L. J. Am. Chem. Soc. 2008, 130, 2422. doi: 10.1021/ja078251w pmid: 18251543
[15]	Soh, J. Y.-T.; Tan, C.-H. J. Am. Chem. Soc. 2009, 131, 6904 doi: 10.1021/ja900582a
[16]	Bartelson, K. J.; Singh, R. P.; Foxman, B. M.; Deng, L. Chem. Sci. 2011, 2, 1940. pmid: 22174973
[17]	Singleton, D. A.; Thomas, A. A. J. Am. Chem. Soc. 1995, 117, 9357. doi: 10.1021/ja00141a030
[18]	Shi, L.-M. Dong, W.-W.; Tao, H.-Y.; Dong, X.-Q.; Wang, C.-J. Org. Lett. 2017, 19, 4532. doi: 10.1021/acs.orglett.7b02107
[19]	Suzuki, T.; Watanabe, S.; Kobayashi, S.; Tanino, K. Org. Lett. 2017, 19, 922. doi: 10.1021/acs.orglett.7b00085
[20]	Toyota, M.; Yoshida, T.; Kan, Y.; Takaoka, S.; Asakawa, Y. Tetrahedron Lett. 1996, 37, 4745. doi: 10.1016/0040-4039(96)00956-2
[21]	Zhao, P.; Beaudry, C. M. Angew. Chem., Int. Ed. 2014, 53, 10500. doi: 10.1002/anie.201406621
[22]	Adolf, W.; Hecker, E. Isr. J. Chem. 1977, 16, 75. doi: 10.1002/ijch.v16:1
[23]	Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2020, 83, 770. doi: 10.1021/acs.jnatprod.9b01285 pmid: 32162523
[24]	(a) Wender, P. A.; Kogen, H.; Lee, H. Y.; Munger, J. D., Jr.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957. doi: 10.1021/ja00206a050 pmid: 18451298
	(b) Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. doi: 10.1021/ja00168a050 pmid: 18451298
	(c) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897. doi: 10.1021/ja9706256 pmid: 18451298
	(d) Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976. doi: 10.1021/ja972279y pmid: 18451298
	(e) Wender, P. A.; Kee, J.-M.; Warrington, J. M. Science 2008, 320, 649. doi: 10.1126/science.1154690 pmid: 18451298
[25]	Lee, K.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 5590. pmid: 11389648
[26]	Kawamura, S.; Chu, H.; Felding, J.; Baran, P. S. Nature 2016, 532, 90. doi: 10.1038/nature17153
[27]	(a) Tong, G.; Liu, Z.; Li, P. Chem 2018, 4, 2944. doi: 10.1016/j.chempr.2018.10.002
	(b) Tong, G.; Ding, Z.; Liu, Z.; Ding, Y.-S.; Xu, L.; Zhang, H.; Li, P. J. Org. Chem. 2020, 85, 4813. doi: 10.1021/acs.joc.0c00022
	(c) Ding, Z.; Liu, Z.; Tong, G.; Hu, L.; He, Y.; Bao, Y.; Lei, Z.; Zhang, H.; Li, P. Org. Chem. Front. 2020, 7, 1862. doi: 10.1039/D0QO00424C
[28]	Yu, T.; Sun, Y.; Tu, C.; Chen, T.; Fu, S.; Liu, B. Chem. Sci. 2020, 11, 7177. doi: 10.1039/D0SC02829K
[29]	(a) Asaba, T.; Katoh, Y.; Urabe, D.; Inoue, M. Angew. Chem., Int. Ed. 2015, 54, 14457. doi: 10.1002/anie.v54.48 pmid: 29041773
	(b) Urabe, D.; Asaba, T.; Inoue, M. Bull. Chem. Soc. Jpn. 2016, 89, 1137. doi: 10.1246/bcsj.20160208 pmid: 29041773
	(c) Hashimoto, S.; Katoh, S.; Kato, T.; Urabe, D.; Inoue, M. J. Am. Chem. Soc. 2017, 139, 16420. doi: 10.1021/jacs.7b10177 pmid: 29041773
[30]	Hirose, A.; Watanabe, A.; Ogino, K.; Nagatomo, M.; Inoue, M. J. Am. Chem. Soc. 2021, 143, 12387. doi: 10.1021/jacs.1c06450
[31]	(a) Oppolzer, W. Angew. Chem., Int. Ed. 1984, 23, 876. doi: 10.1002/(ISSN)1521-3773
	(b) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. doi: 10.1021/cr00013a013
	(c) Notz, W.; Tanaka, F.; Barbas, C. F. Acc. Chem. Res. 2004, 37, 580. doi: 10.1021/ar0300468
[32]	Markό, I. E.; Evans, G. R. Tetrahedron Lett. 1994, 35, 2771.
[33]	Posner, G. H.; Eydoux, F.; Lee, J. K.; Bull, D. S. Tetrahedron Lett. 1994, 35, 7541. doi: 10.1016/S0040-4039(00)78338-9
[34]	(a) Lythgoe, B. Chem. Soc. Rev. 1980, 449.
	(b) Kocienski, P. J.; Lythgoe, B. V. J. Chem. Soc., Perkin Trans. 1 1980, 1400.
[35]	Markό, I. E.; Warriner, S. L.; Augustyns, B. Org. Lett. 2000, 2, 3123. doi: 10.1021/ol006324+
[36]	Liao, S.; Sun, X.-L.; Tang, Y. Acc. Chem. Res. 2014, 47, 2260. doi: 10.1021/ar800104y
[37]	Burch, P.; Binaghi, M.; Scherer, M.; Wentzel, C.; Bossert, D.; Eberhardt, L.; Neuburger, M.; Scheiffele, P.; Gademann, K. Chem.- Eur. J. 2013, 19, 2589. doi: 10.1002/chem.201203746
[38]	(a) Gibson, D. T.; Koch, J. R.; Kallio, R. E. Biochemistry 1968, 7, 2653. pmid: 5722247
	(b) Gibson, D. T.; Koch, J. R.; Schuld, C. L.; Kallio, R. E. Biochemistry 1968, 7, 3795. pmid: 5722247
[39]	(a) Duchek, J.; Adams, D. R.; Hudlicky, T. Chem. Rev. 2011, 111, 4223. doi: 10.1021/cr1004138 pmid: 30613812
	(b) Reed, J. W.; Hudlicky, T. Acc. Chem. Res. 2015, 48, 674. doi: 10.1021/ar500427k pmid: 30613812
	(c) Hudlicky, T. ACS Omega 2018, 3, 17326. doi: 10.1021/acsomega.8b02994 pmid: 30613812
[40]	Liang, X.-W.; Zhao, Y.; Si, X.-G.; Xu, M.-M.; Tan, J.-H.; Zhang, Z.-M.; Zheng, C.-G.; Zheng, C.; Cai, Q. Angew. Chem., Int. Ed. 2019, 58, 14562. doi: 10.1002/anie.v58.41
[41]	For selected reviews, see: Li, G.; Kusari, S.; Spiteller, M. Nat. Prod. Rep. 2014, 31, 1175. doi: 10.1039/C4NP00031E pmid: 25514696
	(b) Schnermann, M. J.; Shenvi, R. A. Nat. Prod. Rep. 2015, 32, 543. doi: 10.1039/c4np00109e pmid: 25514696
[42]	(a) Singh, V.; Iyer, S. R.; Pal, S. Tetrahedron 2005, 61, 9197. doi: 10.1016/j.tet.2005.06.102 pmid: 25891138
	(b) Dhambri, S.; Mohammad, S.; Nguyen Van Buu, O.; Galvani, G.; Meyer, Y.; Lannou, M.-I.; Sorin, G.; Ardisson, J. Nat. Prod. Rep. 2015, 32, 841. doi: 10.1039/c4np00142g pmid: 25891138
[43]	Si, X.-G.; Zhang, Z.-M.; Zheng, C.-G.; Li, Z.-T.; Cai, Q. Angew. Chem., Int. Ed. 2020, 59, 18412. doi: 10.1002/anie.v59.42
[44]	Xu, M.-M.; You, X.-Y.; Zhang, Y.-Z.; Lu, Y.; Yang, L.-M.; Cai, Q. J. Am. Chem. Soc. 2021, 143, 8993. doi: 10.1021/jacs.1c04759
[45]	Zhou, Y.; Zhou, Z.; Du, W.; Chen, Y. Acta Chim. Sinica 2018, 76, 382. (in Chinese) doi: 10.6023/A18040131
	(周远春, 周志, 杜玮, 陈应春, 化学学报, 2018, 76, 382.) doi: 10.6023/A18040131
[46]	Cole, C.; Fuentes, L.; Snyder, S. A. Chem. Sci. 2020, 11, 2175. doi: 10.1039/C9SC05738B

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