Total synthesis of cis-solamin A, a mono-tetrahydrofuran acetogenin isolated from Annona muricata

Tetrahedron Letters

Volumn 49, Issue 5, 2008, Pages 782-785

  Konno, Hiroyuki ^a   Okuno, Yasuhiro ^b   Makabe, Hidefumi ^c   Nosaka, Kazuto ^a   Onishi, Akio ^a   Abe, Yoshinari ^a   Sugimoto, Atsuya ^a   Akaji, Kenichi ^a  

^a KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

^c SHINSHU UNIVERSITY   (Japan)

Author keywords

Annonaceous acetogenin; Cross metathesis; Enzymatic transesterification; Mitochondrial complex I inhibitor; Solamin

Indexed keywords

ACETOGENIN; GAMMA LACTAM DERIVATIVE; SOLAMIN A; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; OPTICS; RING CLOSING METATHESIS;

ANNONA MURICATA;

EID: 37649006222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.190     Document Type: Article

References (47)

1. For recent reviews, see:. Bermejo A., Figadere B., Zafra-Polo M.C., Barrachina I., Estornell E., and Cortes D. Nat. Prod. Rep. 22 (2005) 269-303
2. Makabe, H.; Konno, H.; Miyoshi, H. Curr. Drug Discovery Technol., in press.
3. For recent synthetic studies, see:. Hattori Y., Konno H., Abe M., Miyoshi H., Goto T., and Makabe H. Bioorg. Med. Chem. 15 (2007) 3026-3031
4. Keaton K.A., and Phillips A.J. J. Am. Chem. Soc. 128 (2006) 408-409
5. Curran D.P., Zhang Q., Richard C., Lu H., Gudipati V., and Wilcox C.S. J. Am. Chem. Soc. 128 (2006) 9561-9573
6. Pinacho C.F.R., Carrillo R., Leon L.G., Martin T., Padron J.M., and Martin V.S. J. Org. Chem. 71 (2006) 2339-2345
7. Narayan R.S., and Borhan B. J. Org. Chem. 71 (2006) 1416-1429
8. Crimmins M.T., Zhang Y., and Diaz F.A. Org. Lett. 8 (2006) 2369-2372
9. Hoye T.R., Eklov B.M., Jeon J., and Khoroosi M. Org. Lett. 8 (2006) 3383-3386
10. Makabe H., Higuchi M., Konno H., Murai M., and Miyoshi H. Tetrahedron Lett. 46 (2005) 4671-4675 and references cited therein
11. Murai M., Ishihara A., Nishioka T., Yagi T., and Miyoshi H. Biochemistry 46 (2007) 6409-6416
12. Murai M., Ichimaru N., Abe M., Nishioka T., and Miyoshi H. Biochemistry 45 (2006) 9778-9787
13. Derbré S., Roué G., Poupon E., Susin S.A., and Hocquenmiller R. ChemBioChem 6 (2005) 979-982
14. Ichimaru N., Murai M., Abe M., Hamada T., Yamada Y., Makino S., Nishioka T., Makabe H., Makino A., Kobayashi T., and Miyoshi H. Biochemistry 44 (2005) 816-825
15. Li H.-X., Huang G.-R., Zhang H.-M., Jiang S., Wu J.-R., and Yao Z.-J. ChemBioChem 8 (2007) 172-177
16. Barrachina J., Royo I., Baldoni H.A., Chahboune N., Suyire F., DePedro N., Zafra-Polo M.C., Bermejo A., El Aouad N., Cabedo N., Saez J., Tormo J.R., Enriz R.D., and Cortes D. Bioorg. Med. Chem. 15 (2007) 4369-4381
17. Gleye C., Duret P., Laurens A., Hocquemiller R., and Cavé A. J. Nat. Prod. 61 (1998) 567-579
18. Göksel H., and Stark C.B.W. Org. Lett. 8 (2006) 3433-3436
19. Donohoe T.J., and Butterworth S. Angew. Chem., Int. Ed. 44 (2005) 4766-4768
20. Cecil A.R.L., Hu Y.L., Vicent M.J., Duncan R., and Brown R.C.D. J. Org. Chem. 69 (2004) 3368-3374
21. Cecil A.R.L., and Brown R.C.D. Org. Lett. 4 (2002) 3715-3718
22. Makabe H., Hattori Y., Kimura Y., Konno H., Abe M., Miyoshi H., Tanaka A., and Oritani T. Tetrahedron 60 (2004) 10651-10657
23. Makabe H., Hattori Y., Tanaka A., and Oritani T. Org. Lett. 4 (2002) 1083-1085
24. Hu Y., Cecil A.R.L., Frank X., Gleye C., Figadere B., and Brown R.C.D. Org. Biomol. Chem. 4 (2006) 1217-1219
25. Blackwell H.E., O'Leary D.J., Chatterjee A.K., Washenfelder R.A., Bussmann D.A., and Grubbs R.H. J. Am. Chem. Soc. 122 (2000) 58-71
26. Marshall J.A., Sabatini J.J., and Valeriote E. Bioorg. Med. Chem. Lett. 17 (2007) 2434-2437
27. Takahashi T., Hongo Y., Ogawa N., Koshino H., and Nakata T. J. Org. Chem. 71 (2006) 6305-6308
28. Hoye T.R., Eklov B.M., Jeon J., and Khoroosin M. Org. Lett. 8 (2006) 3383-3386
29. Zhu L., and Mootoo D.R. J. Org. Chem. 69 (2004) 3154-3157
30. Evans P.A., Cui J., Gharpure S.J., Polosukhin A., and Zhang H.-R. J. Am. Chem. Soc. 125 (2003) 14702-14703
31. Baran P.S., Maimone T.J., and Richter J.M. Nature 446 (2007) 404-408
32. Ahmed M.M., Cui H., and O'Doherty G.A. J. Org. Chem. 71 (2006) 6686-6689
33. Dhotare B., and Chattopadhyay A. Tetrahedron Lett. 46 (2005) 3103-3105
34. Quinn K.J., Isaacs A.K., and Arvary R.A. Org. Lett. 6 (2004) 4143-4145
35. Yoshimitsu T., Makino T., and Nagaoka H. J. Org. Chem. 68 (2003) 7548-7550
36. Konno H., Hiura N., and Yanaru M. Heterocycles 57 (2002) 1793-1797
37. Yoshida N., Konno H., Kamikubo T., Takahashi M., and Ogasawara K. Tetrahedron: Asymmetry 10 (1999) 3849-3857
38. Konno H., and Ogasawara K. Synthesis (1999) 1135-1140
39. Kolb H.C., VanNieuwhenze M., and Sharpless K.B. Chem. Rev. 94 (1994) 2483-2547
40. Theil F., and Schick H. Synthesis (1991) 533-535
41. Sugahara T., Kuroyanagi Y., and Ogasawara K. Synthesis (1996) 1101-1108
42. Asymmetric dihydroxylation of trans-3-pentenenitrile provided a 3,4-dihydroxypentanenitrile, which showed 80% ee in a HPLC-based analysis of the corresponding benzoate.
43. Kinetic hydrolysis of the racemic acetate (±-9) with Novozyme in 0.2 M Na-phosphate buffer did not give satisfactory results in terms of yield and enantiomeric excess.
44. Araya H., Hara N., Fujimoto Y., and Sahai M. Biosci., Biotech., Biochem. 58 (1994) 1146-1147
45. Konno H., Makabe H., Tanaka A., and Oritani T. Biosci., Biotech., Biochem. 60 (1996) 526-527
46. Franck X., Figadere B., and Cavé A. Tetrahedron Lett. 37 (1996) 1953-1954 {A figure is presented}
47. Marshall J.A., and Chen M. J. Org. Chem. 62 (1997) 5996-6000