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Synthesis 2022; 54(10): 2415-2422
DOI: 10.1055/a-1730-8628
DOI: 10.1055/a-1730-8628
paper
Total Synthesis of Cryptopleurine and Its Analogues
This work was financially supported by JSPS KAKENHI (Grants 18K05103 and 19H03350), MEXT KAKENHI (Grant JP21H05212) in Digi-TOS, and the AMED Platform for Supporting Drug Discovery and Life Science Research (Grant jp19am0101092j0003). Y.Y. thanks the Takeda Science Foundation for financial support.
Abstract
Total synthesis of phenanthroquinolizidine alkaloid cryptopleurine was achieved in 8 steps from commercially available 2-pyridinecarboxaldehyde and the epoxide derived from methyleugenol. The key intermediate vinyl triflate enables the divergent synthesis of cryptopleurine derivatives by late-stage installation of various substituents on the C-ring.
Key words
heterocycles - phenanthroquinolizidines - cryptopleurine - natural product synthesis - cyclization - anticancer agentsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1730-8628.
- Supporting Information
Publication History
Received: 29 November 2021
Accepted after revision: 04 January 2022
Accepted Manuscript online:
04 January 2022
Article published online:
21 February 2022
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References
- 1a Li Z, Jin Z, Huang R. Synthesis 2001; 2365
- 1b Chemler SR. Curr. Bioact. Compd. 2009; 5: 2
- 1c Burtoloso AC. B, Bertonha AF, Rosset IG. Curr. Bioact. Compd. 2014; 14: 191
- 2 Gao W, Lam W, Zhong S, Kaczmarek C, Baker DC, Cheng Y.-C. Cancer Res. 2004; 64: 678
- 3 Suffness M, Cordell GA. In The Alkaloids Chemistry and Pharmacology, Vol. 25. Brossi A. Academic Press; New York: 1985: 3-355
- 4a Stærk D, Christensen J, Lemmich E, Duus J. Ø, Olsen CE, Jaroszewski JW. J. Nat. Prod. 2000; 63: 1584
- 4b Lykkeberg AK, Christensen J, Budnik BA, Abe F, Jaroszewski JW. J. Nat. Prod. 2002; 65: 1299
- 5a Chuang T.-H, Lee S.-J, Yang C.-W, Wu P.-L. Org. Biomol. Chem. 2006; 4: 860
- 5b Gao W, Busson S, Grill SP, Gullen EA, Hu Y.-C, Huang X, Zhong S, Kaczmarek C, Gutierrez J, Francis S, Baker DC, Yu S, Cheng Y.-C. Bioorg. Med. Chem. Lett. 2007; 17: 4338
- 5c Su C.-R, Damu AG, Chiang P.-C, Bastow KF, Morris-Natschke SL, Lee K.-H, Wu T.-S. Bioorg. Med. Chem. 2008; 16: 6233
- 6a Banwell MG, Bezos A, Burns C, Kruszelnicki I, Parish CR, Su S, Sydnes MO. Bioorg. Med. Chem. Lett. 2006; 16: 181
- 6b Wei L, Brossi A, Kendall R, Bastow KF, Morris-Natschke SL, Shi Q, Lee K.-H. Bioorg. Med. Chem. 2006; 14: 6560
- 7a Fu Y, Lee SK, Min H.-Y, Lee T, Lee J, Cheng M, Kim S. Bioorg. Med. Chem. Lett. 2007; 17: 97
- 7b Kwon Y, Song J, Lee H, Kim E.-Y, Lee K, Lee SK, Kim S. J. Med. Chem. 2015; 58: 7749
- 8a Jo Y.-I, Cheon C.-H. J. Org. Chem. 2019; 84: 11902
- 8b Ansari A, Ramapanicker R. ChemistrySelect 2018; 3: 12591
- 8c Lerchen A, Knecht T, Koy M, Daniliuc CG, Glorius F. Chem. Eur. J. 2017; 23: 12149
- 8d Chang C.-F, Li C.-F, Tsai C.-C, Chuang T.-H. Org. Lett. 2016; 18: 638
- 8e Liéby-Muller F, Marion F, Schmitt P, Annereau J, Kruczynski A, Guibaud N, Bailly C. Bioorg. Med. Chem. Lett. 2015; 25: 184
- 8f Stoye A, Opatz T. Eur. J. Org. Chem. 2015; 2149
- 8g Chen F, Su B, Wang Q. Org. Chem. Front. 2014; 1: 674
- 8h Zheng Y, Liu Y, Wang Q. J. Org. Chem. 2014; 79: 3348
- 8i Ying W, Herndon JW. Eur. J. Org. Chem. 2013; 3112
- 8j Pasare SV, Dyapa R. Org. Biomol. Chem. 2012; 10: 6776
- 8k Zeng C, Liu H, Zhang M, Guo J, Jiang S, Yu S. Synlett 2012; 23: 2251
- 8l Wang Z, Feng A, Cui M, Liu Y, Wang L, Wang Q. PloS One 2012; 7: e52933
- 8m Yang X, Shi Q, Bastow KF, Lee K.-H. Org. Lett. 2010; 12: 1416
- 8n Cui M, Song H, Feng A, Wang Z, Wang Q. J. Org. Chem. 2010; 75: 7018
- 8o Wang Z, Wang Q. Tetrahedron Lett. 2010; 51: 1377
- 8p Cui M, Wang Q. Eur. J. Org. Chem. 2009; 5445
- 9a Yamaoka Y, Taniguchi M, Yamada K, Takasu K. Heterocycles 2018; 97: 292
- 9b Yamaoka Y, Taniguchi M, Yamada K, Takasu K. Synthesis 2015; 47: 2819
- 10 Tian G, Song L, Li Z, Robeyns K, Van Meervelt L, Van der Eycken EV. A. Org. Lett. 2020; 22: 8441
- 11 Jeyakumar K, Chand DK. Synthesis 2008; 807
- 12 Koepler O, Laschat S, Baro A, Fischer P, Miehlich B, Hotfilder M, le Viseur C. Eur. J. Org. Chem. 2004; 3611
- 13 Heathcock CH, Norman MH, Dickman DA. J. Org. Chem. 1990; 55: 798
- 14 Even though the smaller 3-methoxy group instead of the 3-tert-butyldimethylsilyloxy group was used in the same reaction, the methoxy group was selectively installed at the 7-position.
- 15 Hobson ST, Boecker JD, Gifford JH, Nohe TL, Wierks CH. J. Heterocycl. Chem. 2003; 40: 277
For reviews of phenanthroindolizidine and phenanthroquinoizidine alkaloids, see:
Recent examples of total synthesis of cryptopleurine, see: