Synthesis of Carbocyclic Nucleosides (+)-Neplanocin A, (+)-Aristeromycin and 4'-epi-(+)-Aristeromycin from D-Fructose

Author(s): Perali R. Sridhar* , Vennam D.K. Reddy , Mandava Suresh , Nadiveedhi M. Reddy , K. Shiva Kumar .

Journal Name: Letters in Organic Chemistry

Volume 16 , Issue 9 , 2019

Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

D-Fructose is used as the chiral pool starting material for the stereoselective total synthesis of (+)-neplanocin A. Zinc mediated fragmentation, ring-closing metathesis and oxidative rearrangement of cyclic tertiary allylic alcohol are used as the key steps in achieving the synthesis of key carbocylic intermediate. Further, stereoselective total synthesis of 4'-epi-(+)-aristeromycin and the conversion of (+)-neplanocin A to a mixture of (+)-aristeromycin and 4'-epi-(+)-aristeromycin are described.

Keywords: Carbocycles, nucleosides, total synthesis, natural products, D-Fructose, metathesis.

[1]
(a) Yaginuma, S.; Muto, N.; Tsujino, M.; Sudate, Y.; Hayashi, M.; Otani, M. J. Antibiot., 1981, 34, 359-366.
(b) Isono, K. J. Antibiot., 1988, 41, 1711-1739.
[2]
(a) Montgomery, J.A. Med. Res. Rev., 1982, 2, 271-308.
(b) Herdewijin, P. Modified Nucleosides.In Biochemistry, Biotechnology and Medicine; Wiley-VCH: Weinheim, 2008.
[3]
(a) Chapleur, Y. Carbohydrate Mimics: Concepts and Methods; Wiley-VCH Verlag GmbH., 1998.
(b) Boutureira, O.; Matheu, M.I.; Díaz, Y.; Castillón, S. Chem. Soc. Rev., 2013, 42, 5056-5072.
[4]
Borthwick, A.D.; Kirk, B.; Biggadike, K.; Exall, A.; Butt, S.; Roberts, S.; Knight, D.; Coates, J.; Ryan, D. J. Med. Chem., 1991, 34, 907-914.
[5]
Price, P.; Banerjee, R.; Jeffrey, A.; Acs, G. Hepatology, 1992, 16, 8-12.
[6]
Slusarchyk, W.A.; Young, M.G.; Bisacchi, G.S.; Hockstein, D.R.; Zahler, R. Tetrahedron Lett., 1989, 30, 6453-6456.
[7]
Hayashi, S.; Norbeck, D.W.; Rosenbrook, W.; Fine, R.L.; Matsukura, M.; Plattner, J.J.; Broder, S.; Mitsuya, H. Antimicrob. Agents Chemother., 1990, 34, 287-294.
[8]
Vince, R.; Hua, M. J. Med. Chem., 1990, 33, 17-21.
[9]
Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St Clair, M.H.; Boone, L.R.; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R. Antimicrob. Agents Chemother., 1997, 41, 1082-1093.
[10]
(a) Marquez, V.E.; Lim, M-I. Med. Res. Rev., 1986, 6, 1-40.
(b) Saunders, J.; Cameron, J.M. Med. Res. Rev., 1995, 15, 497-531.
(c) Roberts, S.M.; Biggadike, K.; Borthwick, A.D.; Kirk, B. In Topics in Medicinal Chemistry; Leeming, P.R., Ed.; Royal Society of Chemistry: London, UK, 1998.
(d) Song, G.Y.; Paul, V.; Choo, H.; Morrey, J.; Sidwell, R.W.; Schinazi, R.F.; Chu, C.K. J. Med. Chem., 2001, 44, 3985-3993.
[11]
Kusuka, T.; Yamamoto, H.; Shibata, M.; Muroi, M.; Kishi, T.; Mizuno, K. J. Antibiot., 1968, 21, 255-263.
[12]
(a) Borchardt, R.T.; Keller, B.T.; Patel-Thombre, U. J. Biol. Chem., 1984, 259, 4353-4358.
(b) Wolfson, G.; Chisholm, J.; Tashjian, A.H.; Fish, S.; Abeles, R.H. J. Biol. Chem., 1986, 261, 4492-4498.
[13]
(a) Song, G.Y.; Paul, V.; Choo, H.; Morrey, J.; Sidwell, R.W.; Schinazi, R.F.; Chu, C.K. J. Med. Chem., 2001, 44, 3985-3993.
(b) Jung, Y.H.; Kim, S.I.; Hong, Y.J.; Park, S.J.; Kang, K.T.; Kim, S.Y.; Kim, I.S. Tetrahedron, 2015, 71, 1068-1073.
[14]
Coates, J.A.V.; Cammack, N.; Jenkinson, H.J.; Mutton, I.M.; Pearson, B.A.; Storer, R.; Cameron, J.M.; Penn, C.R. Antimicrob. Agents Chemother., 1992, 36, 202-205.
[15]
Furman, P.A.; Davis, M.; Liotta, D.C.; Paff, M.; Frick, L.W.; Nelson, D.J.; Dornsife, R.E.; Wurster, J.A.; Wilson, L.J.; Fyfe, J.A.; Tuttle, J.V.; Miller, W.H.; Condreay, L.; Averett, D.R.; Schinazi, R.F.; Painter, G.R. Antimicrob. Agents Chemother., 1992, 36, 2686-2692.
[16]
Lin, T-S.; Luo, M-Z.; Liu, M-C.; Pai, S.B.; Dutschman, G.E.; Cheng, Y-C. J. Med. Chem., 1994, 37, 798-803.
[17]
Chu, C.K.; Ma, T.; Shanmuganathan, K.; Wang, C.; Xiang, Y.; Pai, S.B.; Yao, G-Q.; Sommadossi, J-P.; Cheng, Y-C. Antimicrob. Agents Chemother., 1995, 39, 979-981.
[18]
(a) Wang, P.; Gullen, B.; Newton, M.G.; Cheng, Y-C.; Schinazi, R.F.; Chu, C.K. J. Med. Chem., 1999, 42, 3390-3399.
(b) Lin, T-S.; Luo, M-Z.; Liu, M-C.; Zhu, Y-L.; Gullen, E.; Dutschman, G.E.; Cheng, Y-C. J. Med. Chem., 1996, 39, 1757-1759.
(c) Bolon, P.J.; Wang, P.Y.; Chu, C.K.; Gosselin, G.; Boudou, V.; Pierra, C.; Mathe´, C.; Imbach, J-L.; Faraj, A.; El Alaoui, M.A.; Sommadossi, J-P.; Pai, S.B.; Zhu, Y-L.; Lin, J-S.; Cheng, Y-C.; Schinazi, R.F. Bioorg. Med. Chem. Lett., 1996, 6, 1657-1662.
[19]
(a) Sridhar, P.R.; Suresh, M.; Ramakrishna, B. Tetrahedron, 2011, 67, 4031-4035.
(b) Sridhar, P.R.; Suresh, M.; Sudharani, C. Tetrahedron, 2011, 67, 9283-9290.
(c) Sridhar, P.R.; Suresh, M. Kumar, P.V.; Seshadri, K.; Rao, C.V. Carbohydr. Res., 2012, 360, 40-46.
[20]
(a) Arita, M.; Adachi, K.; Ito, Y.; Sakai, H.; Ohno, M. J. Am. Chem. Soc., 1983, 105, 4049-4055.
(b) Hutchinson, E.J.; Roberts, S.M.; Thorpe, A.J. J. Chem. Soc., Perkin Trans. 1, 1992, 2245-2246.
(c) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett., 1998, 39, 4677-4678.
[21]
(a) Medich, J.R.; Kunnen, K.B.; Johnson, C.R. Tetrahedron Lett., 1987, 28, 4131-4134.
(b) Nokami, J.; Matsuura, H.; Takahashi, H.; Yamashita, M. Synlett, 1994, 1994, 491-493.
[22]
(a) Lim, M-I.; Marquez, V.E. Tetrahedron Lett., 1983, 24, 5559-5562.
(b) Tseng, C.K.H.; Marquez, V.E. Tetrahedron Lett., 1985, 26, 3669-3672.
(c) Marquez, V.E.; Lim, M-I.; Tseng, C.K-H.; Markovac, A.; Priest, M.A.; Khan, M.S.; Kaskar, B. J. Org. Chem., 1988, 53, 5709-5714.
(d) Bestmann, H.J.; Roth, D. Angew. Chem. Int. Ed. Engl., 1990, 29, 99-100.
(e) Wolfe, M.S.; Anderson, B.L.; Borcherding, D.R.; Borchardt, R.T. J. Org. Chem., 1990, 55, 4712-4717.
(f) Hill, J.M.; Hutchinson, E.J.; Le Grand, D.M.; Roberts, S.M.; Thorpe, A.J.; Turner, N.J. J. Chem. Soc., Perkin Trans. 1, 1994, 1483-1487.
(g) Wang, P.; Agrofoglio, L.A.; Newton, M.G.; Chu, C.K. J. Org. Chem., 1999, 64, 4173-4178.
(h) Hegedus, L.S.; Geisler, L. J. Org. Chem., 2000, 65, 4200-4203.
iMichel, B.Y.; Strazewski, P. Tetrahedron, 2007, 63, 9836-9841.
[23]
Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. J. Org. Chem., 2001, 66, 8199-8203.
[24]
Gallos, J.K.; Stathakis, C.I.; Kotoulas, S.S.; Koumbis, A.E. J. Org. Chem., 2005, 70, 6884-6890.
[25]
Tan, Y.X.; Santhanakrishnan, S.; Yang, H.Y.; Chai, C.L.L.; Tam, E.K.W. J. Org. Chem., 2014, 79, 8059-8066.
[26]
(a) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett., 1995, 36, 1537-1538.
(b) Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron, 1997, 53, 13621-13632.
[27]
Cho, J.H.; Bernard, D.L.; Sidwell, R.W.; Kern, E.R.; Chu, C.K. J. Med. Chem., 2006, 49, 1140-1148.
[28]
(a) Trost, B.M.; Madsen, R.; Guile, S.D. Tetrahedron Lett., 1997, 38, 1707-1710.
(b) Trost, B.M.; Madsen, R.; Guile, S.D.; Brown, B. J. Am. Chem. Soc., 2000, 122, 5947-5956.
[29]
(a) Choi, W.J.; Moon, H.R.; Kim, H.O.; Ko, Y.M.; Kim, H.J.; Lee, J.A.; Lee, K.M.; Yun, M.K.; Shin, D.H. Chun. M.W.; Sheen, Y.Y.; Kim, K.; Jeong, L.S. Nucleotides Nucleic Acids, 2005, 24, 611-613.
(b) Michel, B.Y.; Strazewski, P. Tetrahedron, 2007, 63, 9836-9841.
[30]
Paquette, L.A.; Tian, Z.; Seekamp, C.K.; Wang, T. Helv. Chim. Acta, 2005, 88, 1185-1198.
[31]
(a) Dey, S.; Garner, P. J. Org. Chem., 2000, 65, 7697-7699.
(b) Raymond, C.F.J.; Lisa, J.C.; James, N.I. ARKIVOC, 2011, 82-103.
[32]
(a) Ye, W.; Schneller, S.W. J. Org. Chem., 2006, 71, 8641-8643.
(b) Ainai, T.; Wang, Y-G.; Tokoro, Y.; Kobayashi, Y. J. Org. Chem., 2004, 69, 655-659.
(c) Brown, B.; Hegedus, L.S. J. Org. Chem., 2000, 65, 1865-1872.
(d) Tokoro, Y.; Kobayashi, Y. Chem. Commun., 1999, 9, 807-809.
(e) Csuk, R.; Dörr, P. Tetrahedron, 1995, 51, 5789-5798.
(f) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc. Chem. Commun., 1992, 1454-1455.
(g) Trost, B.M.; Li, L.; Guile, S.D. J. Am. Chem. Soc., 1992, 114, 8745-8747.
(h) Yoshikawa, M.; Okaichi, Y.; Cha, B.C.; Kitagawa, I. Tetrahedron, 1990, 46, 7459-7470.
(i) Wolfe, M.S.; Anderson, B.L.; Borcherding, D.R.; Borchardt, R.T. J. Org. Chem., 1990, 55, 4712-4717.
(j) Madhavan, G.V.B.; Martin, J.C. J. Org. Chem., 1986, 51, 1287-1293.
(k) Wang, P.; Agrofoglio, L.A.; Newton, M.G.; Chu, C.K. Tetrahedron Lett., 1997, 38, 4207-4210.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 16
ISSUE: 9
Year: 2019
Page: [750 - 758]
Pages: 9
DOI: 10.2174/1570178615666181023145502
Price: $58

Article Metrics

PDF: 16
HTML: 2