Aza-Wacker Cyclization Toward the Bridged Core of FR901483

Defeng Shen; Changmin Xie; Zhuwei Ruan; Chen Yang; Sha-Hua Huang; Lili Zhu; Ran Hong

doi:10.1055/a-2012-5187

Synthesis, Table of Contents

Synthesis 2023; 55(12): 1940-1948
DOI: 10.1055/a-2012-5187

paper

Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry

Aza-Wacker Cyclization Toward the Bridged Core of FR901483

Authors

Defeng Shen

^aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Changmin Xie

^aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Zhuwei Ruan

^aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Chen Yang

^aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Sha-Hua Huang

^bSchool of Environmental and Chemical Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
Lili Zhu∗

^aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Ran Hong∗

^aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

Abstract

All articles of this category

Abstract

A nine-step synthetic route to access the tricyclic core of FR901483 is reported, featuring a key aza-Wacker cyclization step to construct an α-tertiary amine (ATA) in the bridged structure. The aza-Wacker protocol can tolerate both exocyclic and endocyclic double bonds, providing viable access to various bridged bicyclic rings bearing an ATA (e.g., 6-azabicyclo[3.2.1]octane, 7-azabicyclo[3.3.1]nonane, and 7-azabicyclo[4.2.1]nonane) in good to excellent yields. The synthetic studies presented herein enable structural derivatization of FR901483 to further exploit its compelling biological activities.

Key words

aza-Wacker - bridged system - FR901483 - immunosuppressant - α-tertiary amine

Full Text

References

References
1 Hager A, Vrielink N, Hager D, Lefranc J, Trauner D. Nat. Prod. Rep. 2016; 33: 491
2 Alvandi F, Kwitkowski VE, Ko C.-W, Rothmann MD, Ricci S, Saber H, Ghosh D, Brown J, Pfeiler E, Chikhale E, Grillo J, Bullock J, Kane R, Kaminskas E, Farrell AT, Pazdur R. Oncologist 2014; 19: 94

For reviews on the synthesis of cephalotaxine, see:

3a Jeon H. Asian J. Org. Chem. 2021; 10: 3052
3b Pérard-Viret J, Quteishat L, Alsalim R, Royer J, Dumas F. Cephalotaxus Alkaloids. In The Alkaloids: Chemistry and Biology, Vol. 78. Knölker H.-J. Academic Press; New York: 2017: 205-352

4 Blackman AJ, Hambley TW, Picker K, Taylor WC, Thirasasana N. Tetrahedron Lett. 1987; 28: 5561

5a Ruan Z, Zhu L, Zheng K, Hong R. Tetrahedron Lett. 2021; 67: e152880
5b Rohini R, Reddy MP, Shanker K, Hu A, Ravinder V. Eur. J. Med. Chem. 2010; 45: 1200

6a Cimino G, De Stefano S, Scognamiglio G, Sodano G, Trivellone E. Bull. Soc. Chim. Belg. 1986; 95: 783
6b Cimino G, Mattia CA, Mazzarella L, Puliti R, Scognamiglio G, Spinella A, Trivellone E. Tetrahedron 1989; 45: 3863

7a Higo T, Ukegawa T, Yokoshima S, Fukuyama T. Angew. Chem. Int. Ed. 2015; 54: 7367
7b Becker MH, Chua P, Downham R, Douglas CJ, Garg NK, Hiebert S, Jaroch S, Matsuoka RT, Middleton JA, Ng FW, Overman LE. J. Am. Chem. Soc. 2007; 129: 11987
7c Garg NK, Hiebert S, Overman LE. Angew. Chem. Int. Ed. 2006; 45: 2912

8a Baldwin JE, Whitehead RC. Tetrahedron Lett. 1992; 33: 2059
8b Delpech B. The Saraine Alkaloids. In The Alkaloids: Chemistry and Biology, Vol. 73. Knölker H.-J. Academic Press; New York: 2014: 223-329
8c Tang Y, Zhu L, Hong R. Tetrahedron Chem 2022; 3: e100025

9a Ruan Z, Wang M, Yang C, Zhu L, Su Z, Hong R. JACS Au 2022; 2: 793
9b Liu Y, Ruan Z, Wang Y, Huang S.-H, Hong R. Tetrahedron Lett. 2019; 75: 1767
9c Zhai L, Tian X, Wang C, Cui Q, Li W, Huang S.-H, Yu Z.-X, Hong R. Angew. Chem. Int. Ed. 2017; 56: 11599
9d Ouyang J, Mi X, Wang Y, Hong R. Synlett 2017; 28: 762
9e Huang S.-H, Tian X, Mi X, Wang Y, Hong R. Tetrahedron Lett. 2015; 56: 6656
9f Liu H, Yu J, Li X, Yan R, Xiao J.-C, Hong R. Org. Lett. 2015; 17: 4444
9g Ouyang J, Yan R, Mi X, Hong R. Angew. Chem. Int. Ed. 2015; 54: 10940

10 Sakamoto K, Tsujii E, Abe F, Nakanishi T, Yamashita M, Shigematsu N, Izumi S, Okuhara M. J. Antibiot. 1996; 49: 37
11 Mann J. Nat. Prod. Rep. 2001; 18: 417
12 For a recent review, see: Ruan Z.-W, Li C, Shen D.-F, Huang S.-H, Hong R. Synthesis 2019; 51: 2237

For the total synthesis of FR901483, see:

13a Reich D, Trowbridge A, Gaunt MJ. Angew. Chem. Int. Ed. 2020; 59: 2256
13b Huo H.-H, Xia X.-E, Zhang H.-K, Huang P.-Q. J. Org. Chem. 2013; 78: 455
13c Ma A.-J, Tu Y.-Q, Peng J.-B, Dou Q.-Y, Hou S.-H, Zhang F.-M, Wang S.-H. Org. Lett. 2012; 14: 3604
13d Ieda S, Asoh Y, Fujimoto T, Kitaoka H, Kan T, Fukuyama T. Heterocycles 2009; 79: 721
13e Kan T, Fujimoto T, Ieda S, Asoh Y, Kitaoka H, Fukuyama T. Org. Lett. 2004; 6: 2729
13f Ousmer M, Braun NA, Ciufolini MA. Org. Lett. 2001; 3: 765
13g Ousmer M, Braun NA, Perrin M, Ciufolini MA. J. Am. Chem. Soc. 2001; 123: 7534
13h Maeng JH, Funk RL. Org. Lett. 2001; 3: 1125
13i Scheffler G, Seike H, Sorensen EJ. Angew. Chem. Int. Ed. 2000; 39: 4593
13j Snider BB, Lin H. J. Am. Chem. Soc. 1999; 121: 7778

For the formal synthesis of FR901483, see:

14a Huo H.-H, Zhang H.-K, Xia X.-E, Huang P.-Q. Org. Lett. 2012; 14: 4834
14b Ieda S, Masuda A, Kariyama M, Wakimoto T, Asakawa T, Fukuyama T, Kan T. Heterocycles 2012; 86: 1071
14c Ieda S, Kan T, Fukuyama T. Tetrahedron Lett. 2010; 51: 4027
14d Carson CA, Kerr MA. Org. Lett. 2009; 11: 777
14e Hong S.-P, Brummond KM. J. Org. Chem. 2005; 70: 907
14f Lu J.-L, Brummond KM. Org. Lett. 2001; 3: 1347

For the skeleton synthesis of FR901483, see:

15a Li B.-L, Gao W.-Y, Li H, Zhang S.-Q, Han X.-Q, Lu J, Liang R.-X, Hong X, Jia Y.-X. Chin. J. Chem. 2019; 37: 63
15b Diaba F, Martínez-Laporta A, Bonjoch J. J. Org. Chem. 2014; 79: 9365
15c Perreault S, Rovis T. Synthesis 2013; 45: 719
15d Seike H, Sorensen EJ. Synlett 2008; 695
15e Diaba F, Ricou E, Solé D, Teixidó E, Valls N, Bonjoch J. ARKIVOC 2007; (iv): 320
15f Asari A, Angelow P, Auty JM, Hayes CJ. Tetrahedron Lett. 2007; 48: 2631
15g Simila ST. M, Martin SF. J. Org. Chem. 2007; 72: 5342
15h Kaden S, Reissing HU. Org. Lett. 2006; 8: 4763
15i Simila ST. M, Reichelt A, Martin SF. Tetrahedron Lett. 2006; 47: 2933
15j Kropf JE, Meigh IC, Bebbington MW. P, Weinreb SM. J. Org. Chem. 2006; 71: 2046
15k Bonjoch J, Diaba F, Puigbo G, Peidro E, Sole D. Tetrahedron Lett. 2003; 44: 8387
15l Wardrop DJ, Zhang W.-M. Org. Lett. 2001; 3: 2353
15m Suzuki H, Yamazaki N, Kibayashi C. Tetrahedron Lett. 2001; 42: 3013

16 Schneider G, Neidhart W, Giller T, Schmid G. Angew. Chem. Int. Ed. 1999; 38: 2894
17 Thomas A, Nagamalla S, Sathyamoorthi S. Chem. Sci. 2020; 11: 8073

18a Xie C, Luo J, Zhang Y, Huang S.-H, Zhu L, Hong R. Org. Lett. 2018; 20: 2386
18b Luo J, Xie C, Zhang Y, Huang S.-H, Zhu L, Hong R. Tetrahedron 2018; 74: 5791

19 Nishkimi Y, Iimori T, Sodeoka M, Shibasaki M. J. Org. Chem. 1989; 54: 3354
20 Keck GE, McHardy SF, Wager TT. Tetrahedron Lett. 1995; 36: 7419
21 See the Supporting Information for details
22 Davis FA, Chen B.-C. Chem. Rev. 1992; 92: 919
23 Jing P, Yang Z, Zhao C.-G, Zheng H.-Ji, Fang B.-W, Xie X.-G, She X.-G. Chem. Eur. J. 2012; 18: 6729
24 Wagnières O, Xu Z.-R, Wang Q, Zhu J.-P. J. Am. Chem. Soc. 2014; 136: 15102
25 Nakazawa N, Tagami K, Iimori H, Sano S, Ishikawa T, Nagao Y. Hetereocycles 2001; 55: 2157
26 Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M. Chem. Rev. 2008; 108: 3795
27 Yamamoto Y, Fujikawa R, Umemoto T, Miyaura N. Tetrahedron 2004; 60: 10695

For recent reviews on the bridged ring systems, see:

28a Wang L, Zhang Z, Han H, Liu X, Bu Z, Wang Q. Chin. J. Org. Chem. 2021; 41: 12
28b Wu T, Tang W.-J. Chem. Eur. J. 2021; 27: 3944

29 Zhai L, Tang Y, Zhang Y, Huang S.-H, Zhu L, Hong R. Chem. Rec. 2022; 22: e202100197
30 Allin SM, Duffy LJ, Towler JM. R, Page PC. B, Elsegood MR. J, Saha B. Tetrahedron 2009; 65: 10230

Supplementary Material

Supporting Information (PDF)