Recent Advances in the Total Synthesis of Cephalotane-Type Norditerpenoids from Cephalotaxus sinensis

Hongyi Zhao; Huanhuan Pan; Yi Yao; Jian Huang; Yang Chen

doi:10.1055/a-1828-2170

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(15): 3317-3327
DOI: 10.1055/a-1828-2170

short review

Recent Advances in the Total Synthesis of Cephalotane-Type Norditerpenoids from Cephalotaxus sinensis

Hongyi Zhao

^aState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. of China

,

Huanhuan Pan

^aState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. of China

,

Yi Yao

^bGuizhou Engineering Laboratory for Synthetic Drugs, School of Pharmaceutical Sciences, Guizhou University, Guiyang 550025, P. R. of China

,

Jian Huang∗

^aState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. of China

,

Yang Chen∗

^aState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. of China

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Abstract

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Abstract

Cephalotaxus diterpenoids are well known for their unique structures and biological activities. Cephanolides, as new cephalotane-type norditerpenoids isolated from Cephalotaxus sinensis, have attracted considerable attention from the synthetic community. The present Short Review summarizes strategic approaches toward the total synthesis of cephanolides from 2018 to 2021.

1 Introduction

2 Synthetic Approaches toward Cephalotane-Type Norditerpenoids

2.1 First Total Synthesis of Cephanolides B and C by Zhao (2018)

2.2 Total Synthesis of Cephanolides A–D by Sarpong (2021)

2.3 Total Synthesis of Cephanolide B by Yang (2021)

2.4 Asymmetric Total Synthesis of Cephanolide A by Gao (2020)

2.5 Asymmetric Total Synthesis of Cephanolide B by Gao (2021)

2.6 Asymmetric Total Synthesis of Cephanolides A and B by Cai (2021)

3 Conclusion and Perspectives

Key words

cephalotane-type - norditerpenoids - total synthesis - cephanolides - Cephalotaxus

Volltext

Referenzen

References

1a Atanasov AG, Zotchev SB, Dirsch VM, Supuran CT. Nat. Rev. Drug Discov. 2021; 20: 200
1b Harvey AL. Drug Discovery Today 2008; 13: 894
1c Newman DJ, Cragg GM. J. Nat. Prod. 2020; 83: 770

2 Abdelkafi H, Nay B. Nat. Prod. Rep. 2012; 29: 845
3 Hao DC, Hou XD, Gu XJ, Xiao PG, Ge G.-B. Chin. J. Nat. Med. 2021; 19: 321

4a Mikolajczak KL, Smith CR, Weisleder D. J. Med. Chem. 1977; 20: 328
4b Perard-Viret J, Quteishat L, Alsalim R, Royer J, Dumas F. The Alkaloids: Chemistry and Biology, Vol. 78. Knölker HJ. Academic Press; Cambridge: 2017: 205

5 Xu J, Fan Y, Gan L, Zhou Y, Li J, Yue J. Chem. Eur. J. 2016; 22: 14648
6 Paudler WW, Kerley GI, McKay J. J. Org. Chem. 1963; 28: 2194
7 Kantarjian HM, O’Brien S, Cortes J. Clin. Lymphoma, Myeloma Leuk. 2013; 13: 530
8 Jeon H. Asian J. Org. Chem. 2021; 10: 3052

9a Auerbach J, Weinreb SM. J. Am. Chem. Soc. 1972; 94: 7172
9b Weinreb SM, Auerbach J. J. Am. Chem. Soc. 1975; 97: 2503

10a Semmelhack MF, Chong BP, Jones LD. J. Am. Chem. Soc. 1972; 94: 8629
10b Semmelhack MF, Chong BP, Stauffer RD, Rogerson TD, Chong A, Jones LD. J. Am. Chem. Soc. 1975; 97: 2507

11 Chen Y, Li W. Youji Huaxue 2017; 37: 1885
12 Chang Y, Meng FC, Wang R, Wang CM, Lue XY, Zhang QW. Stud. Nat. Prod. Chem. 2017; 53: 339
13 Buta JG, Flippen JL, Lusby WR. J. Org. Chem. 1978; 43: 1002
14 Kang SQ, Cai SY, Teng L. Acta Pharm. Sinica 1981; 16: 867

15a Li YW, Huang L. Chin. Chem. Lett. 2002; 13: 937
15b Li YW, Zhu LY, Huang L. Chin. Chem. Lett. 2004; 15: 397
15c Yu XM, Chen SZ, Huang L. Chin. Chem. Lett. 2000; 11: 295
15d Yu XM, Zhang LY, Chen SZ, Huang L. Chin. Chem. Lett. 1999; 10: 657
15e Zhang LY, Chen SZ, Wei D, Huang L, Chai JJ, He CH. Chin. Chem. Lett. 1996; 7: 892
15f Zhang LY, Yang WQ, Chen SZ, Huang L. Chin. Chem. Lett. 1997; 8: 15

16 Hegde V, Campitelli M, Quinn RJ, Camp D. Org. Biomol. Chem. 2011; 9: 4570
17 Li W. Asian J. Chem. 2012; 24: 1411

18a Abdelkafi H, Evanno L, Deville A, Dubost L, Chiaroni A, Nay B. Eur. J. Org. Chem. 2011; 2789
18b Abdelkafi H, Evanno L, Herson P, Nay B. Tetrahedron Lett. 2011; 52: 3447
18c Abdelkafi H, Herson P, Nay B. Org. Lett. 2012; 14: 1270
18d Evanno L, Deville A, Dubost L, Chiaroni A, Bodo B, Nay B. Tetrahedron Lett. 2007; 48: 2893

19a Frey B, Mander LN, Hockless DC. R. J. Chem. Soc., Perkin Trans. 1 1998; 1555
19b Frey B, Wells AP, Roden F, Au TD, Hockless DC, Willis AC, Mander LN. Aust. J. Chem. 2000; 53: 819
19c Frey B, Wells AP, Rogers DH, Mander LN. J. Am. Chem. Soc. 1998; 120: 1914
19d Mander L, O’Sullivan T. Synlett 2003; 1367
19e O’Sullivan TP, Zhang H, Mander LN. Org. Biomol. Chem. 2007; 5: 2627
19f Rogers DH, Frey B, Roden FS, Russkamp F.-W, Willis AC, Mander LN. Aust. J. Chem. 1999; 52: 1093
19g Rogers DH, Morris JC, Roden FS, Frey B, King GR, Russkamp F.-W, Bell RA, Mander LN. Pure Appl. Chem. 1996; 68: 515
19h Zhang H, Appels DC, Hockless DC. R, Mander LN. Tetrahedron Lett. 1998; 39: 6577

20 Zhang M, Liu N, Tang W. J. Am. Chem. Soc. 2013; 135: 12434
21 Zhang H.-J, Hu L, Ma Z, Li R, Zhang Z, Tao C, Cheng B, Li Y, Wang H, Zhai H. Angew. Chem. Int. Ed. 2016; 55: 11638
22 Shao H, Zhao Y.-M. Total Synthesis of (±)-Cephanolides B and C Enabled by Palladium-Catalyzed Cascade Cyclization and Late-Stage sp³ C–H Bond Oxidation. In Strategies and Tactics in Organic Synthesis, Vol. 14. Harmata M. Academic Press; London: 2019: 159
23 Jiang C, Xue J, Yuan Y, Li Y, Zhao C, Jing Q, Zhang X, Yang M, Han T, Bai J, Li Z, Li D, Hua H. Phytochemistry 2021; 192: 112939
24 Fan YY, Xu JB, Liu H.-C, Gan LS, Ding J, Yue JM. J. Nat. Prod. 2017; 80: 3159
25 Ge Z, Fan Y, Deng W, Zheng C, Li T, Yue J. Angew. Chem. Int. Ed. 2021; 60: 9374

26a Ni L, Zhong XH, Chen XJ, Zhang BJ, Bao MF, Cai XH. Phytochemistry 2018; 151: 50
26b Ni L, Zhong X, Cai J, Bao M, Zhang B, Wu J, Cai X. Nat. Prod. Bioprospect. 2016; 6: 149

27 Xu L, Wang C, Gao Z, Zhao YM. J. Am. Chem. Soc. 2018; 140: 5653
28 Haider M, Sennari G, Eggert A, Sarpong R. J. Am. Chem. Soc. 2021; 143: 2710
29 Ren Z, Sun Z, Li Y, Fan X, Dai M, Wang Y, Hu X. Angew. Chem. Int. Ed. 2021; 60: 18572
30 Li A, He Z, Liu B, Yang Z, Zhang Z. Org. Lett. 2021; 23: 9237

31a Zhang H, He H, Gao S. Angew. Chem. Int. Ed. 2020; 59: 20417
31b Zhang H, He H, Gao S. Org. Chem. Front. 2021; 8: 555

32 Lu Y, Xu M.-M, Zhang Z.-M, Zhang J, Cai Q. Angew. Chem. Int. Ed. 2021; 60: 26610
33 Barnych B, Vatèle J.-M. Synlett 2011; 1912
34 de Armas P, Carrau R, Concepción JI, Francisco CG, Hernández R, Suárez E. Tetrahedron Lett. 1985; 26: 2493
35 Johnson KF, Schneider EA, Schumacher BP, Ellern A, Scanlon JD, Stanley LM. Chem. Eur. J. 2016; 22: 15619
36 Crabtree RH, Davis MW. J. Org. Chem. 1986; 51: 2655