Examination of Diels–Alder/Tsuji–Trost Route towards Kopsia Alkaloids

Ekaterina A. Zhigileva; Marina V. Molchanova; Pavel N. Solyev; Alexander A. Korlyukov; Mikhail S. Baranov; Andrey A. Mikhaylov

doi:10.1055/a-2186-7034

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(02): 346-356
DOI: 10.1055/a-2186-7034

paper

Examination of Diels–Alder/Tsuji–Trost Route towards Kopsia Alkaloids

Ekaterina A. Zhigileva

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russian Federation

^bLomonosov Moscow State University, Leninskie Gory 1 (3), Moscow 119991, Russian Federation

,

Marina V. Molchanova

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russian Federation

^bLomonosov Moscow State University, Leninskie Gory 1 (3), Moscow 119991, Russian Federation

,

Pavel N. Solyev

^cEngelhardt Institute of Molecular Biology of the Russian Academy of Sciences, 32 Vavilova St., Moscow 119991, Russian Federation

,

Alexander A. Korlyukov

^dNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 119334, Russian Federation

^ePirogov Russian National Research Medical University, Ostrovitianov 1, Moscow 117997, Russian Federation

,

Mikhail S. Baranov

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russian Federation

^ePirogov Russian National Research Medical University, Ostrovitianov 1, Moscow 117997, Russian Federation

,

Andrey A. Mikhaylov ∗

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russian Federation

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A reaction sequence of Diels–Alder cycloaddition and Tsuji–Trost allylation was examined in terms of its application to the synthesis of kopsinine and the related Kopsia alkaloids. Results of the studies in two synthetic directions are presented herein: 1) synthesis of the properly substituted diene, required for the Diels–Alder step; and 2) model studies and optimization of the key reaction sequence in the absence of side-chain. Details on the challenging introduction of the side-chain into tetrahydrocarboline ketone and its silylation, resulting in rare but unproductive vinylogous Claisen cyclization, and the successful Mannich/Mukaiyama aldol sequence are disclosed in the first direction. In the second direction, the endo-selective Diels–Alder reaction with allyl acrylate and Tsuji–Trost allylation providing incorrect stereochemistry are disclosed. Interaction of both dienes with an alkyne provides carbazoles via Alder–Rickert reaction.

Key words

alkaloids - total synthesis - Diels–Alder reaction - Tsuji–Trost allylation - Alder–Rickert reaction

Volltext

Referenzen

References
1 Dewick PM. Medicinal Natural Products: A Biosynthetic Approach 2009
2 O’Connor SE, Maresh J. J. Nat. Prod. Rep. 2006; 23: 532
3 Kam T.-S, Lim K.-H. Alkaloids of Kopsia. In The Alkaloids:Chemistry and Biology, Vol. 66. Cordell GA. Elsevier; New York: 2008: 1-111
4 Bohannon RA, Miller DG, Diamond HD. Cancer Res. 1963; 23: 613
5 Sirindil F, Weibel JM, Pale P, Blanc A. Nat. Prod. Rep. 2022; 39: 1574
6 David B, Sévenet T, Morgat M, Guénard D, Moisand A, Tollon Y, Thoison O, Wright M. Cell Motil. Cytoskeleton 1994; 28: 317
7 Subramaniam G, Hiraku O, Hayashi M, Koyano T, Komiyama K, Kam T.-S. J. Nat. Prod. 2008; 71: 53
8 Chen J, Yang ML, Zeng J, Gao K. Phytochem. Lett. 2014; 7: 156
9 Saxton JE. Synthesis of the Aspidosperma Alkaloids. In The Alkaloids: Chemistry and Biology, Vol. 50. Cordell GA. Academic Press; San Diego: 1998: 343-376
10 Saya JM, Ruijter E, Orru RV. A. Chem. Eur. J. 2019; 25: 8916
11 Wang N, Jiang X. Chem. Rec. 2021; 21: 295
12 Stork G, Dolfini JE. J. Am. Chem. Soc. 1963; 85: 2872
13 Wang N, Xiao X, Liu C.-X, Yao H, Huang N, Zou K. Adv. Synth. Catal. 2022; 364: 2479
14 Qin B, Wang Y, Wang X, Jia Y. Org. Chem. Front. 2021; 8: 369
15 Kozmin SA, Iwama T, Huang Y, Rawal VH. J. Am. Chem. Soc. 2002; 124: 4628
16 Xie J, Wolfe AL, Boger DL. Org. Lett. 2013; 15: 868
17 Jones SB, Simmons B, Mastracchio A, MacMillan DW. C. Nature 2011; 475: 183
18 Kuehne ME, Seaton PJ. J. Org. Chem. 1985; 50: 4790
19 HeinzGötz P, Bats JW, Fritz H. Liebigs Ann. Chem. 1986; 2065
20 Bleile M, Otto HH. Monatsh. Chem. 2005; 136: 1799
21 Pindur U, Pfeuffer L. Tetrahedron Lett. 1987; 28: 3079
22 Harada S, Morikawa T, Nishida A. Org. Lett. 2013; 15: 5314
23 Qin B, Lu Z, Jia Y. Angew. Chem. Int. Ed. 2022; 61: e202201712
24 Tsuji J, Minami I, Shimizu I. Chem. Lett. 1983; 12: 1325
25 Vulovic B, Gruden-Pavlovic M, Matovic R, Saicic RN. Org. Lett. 2014; 16: 34
26 Braun J, Ariëns MI, Matsuo BT, De Vries S, Van Wordragen ED. H, Ellenbroek BD, Vande Velde CM. L, Orru RV. A, Ruijter E. Org. Lett. 2018; 20: 6611
27 Faltracco M, Sukowski V, Van Druenen M, Hamlin TA, Bickelhaupt FM, Ruijter E. J. Org. Chem. 2020; 85: 9566
28 Li W, Chen Z, Yu D, Peng X, Wen G, Wang S, Xue F, Liu XY, Qin Y. Angew. Chem. Int. Ed. 2019; 58: 6059
29 Chittari P, Thomas A, Rajappa S. Tetrahedron Lett. 1994; 35: 3793
30 Thomas A, Rajappa S. Tetrahedron 1995; 51: 10571
31 Swaney BE, Gai S, Clark MR, Hawkins BC. Chem. Asian J. 2019; 14: 1102
32 Hızlıateş CG, Gülle S. J. Heterocycl. Chem. 2016; 53: 1584
33 Gartshore CJ, Lupton DW. Aust. J. Chem. 2013; 66: 882
34 Li Z, Zhang S, Wu S, Shen X, Zou L, Wang F, Li X, Peng F, Zhang H, Shao Z. Angew. Chem. Int. Ed. 2013; 52: 4117
35 Yasuda M, Chiba K, Ohigashi N, Katoh Y, Baba A. J. Am. Chem. Soc. 2003; 125: 7291
36 Yasuda M, Shigeyoshi Y, Shibata I, Baba A. Synthesis 2005; 233
37 Leng L, Zhou X, Liao Q, Wang F, Song H, Zhang D, Liu XY, Qin Y. Angew. Chem. Int. Ed. 2017; 56: 3703
38 Zhang YA, Milkovits A, Agarawal V, Taylor CA, Snyder SA. Angew. Chem. Int. Ed. 2021; 60: 11127
39 Krapcho AP, Weimaster JF, Eldridge JM, Jahngen EG. E, Lovey AJ, Stephens WP. J. Org. Chem. 1978; 43: 138
40 Azuma T, Takemoto Y, Takasu K. Chem. Pharm. Bull. 2011; 59: 1190
41 Paquette LA, Sivik MR. Synth. Commun. 1991; 21: 467
42 Dilman AD, Ioffe SL. Chem. Rev. 2003; 103: 733
43 Minowa N, Mukaiyama T. Chem. Lett. 1987; 16: 1719
44 Schuppe AW, Liu Y, Gonzalez-Hurtado E, Zhao Y, Jiang X, Ibarraran S, Huang D, Wang X, Lee J, Loria JP, Dixit VD, Li X, Newhouse TR. Chem 2022; 8: 2856
45 Dwulet NC, Chahine Z, Le Roch KG, Vanderwal CD. J. Am. Chem. Soc. 2023; 145: 3716
46 Goh YW, Danczak SM, Lim TK, White JM. J. Org. Chem. 2007; 72: 2929
47 Geng X, Danishefsky SJ. Org. Lett. 2004; 6: 413
48 Yu J, Yang M, Guo Y, Ye T. Org. Lett. 2019; 21: 3670
49 Arcadi A, Cacchi S, Marinelli F, Pace P. Synlett 1993; 743
50 Sha SC, Zhang J, Carroll PJ, Walsh PJ. J. Am. Chem. Soc. 2013; 135: 17602
51 Purgatorio R, de Candia M, Catto M, Carrieri A, Pisani L, De Palma A, Toma M, Ivanova OA, Voskressensky LG, Altomare CD. Eur. J. Med. Chem. 2019; 177: 414
52 Perrotta D, Racine S, Vuilleumier J, De Nanteuil F, Waser J. Org. Lett. 2015; 17: 1030
53 Wenzel AG, Jacobsen EN. J. Am. Chem. Soc. 2002; 124: 12964
54 Klán P, Beňovský P. Monatsh. Chem. 1992; 123: 469
55 Adair GR. A, Edwards MG, Williams JM. J. Tetrahedron Lett 2003; 44: 5523

Zusatzmaterial

Supporting Information