A concise synthesis of solamin and cis-solamin, mono-THF acetogenins from Annona muricata

Heterocycles

Volumn 78, Issue 9, 2009, Pages 2369-2376

  Makabe, Hidefumi ^a   Kuwabara, Asuka ^a   Hattori, Yasunao ^a   Konno, Hiroyuki ^b  

^a SHINSHU UNIVERSITY   (Japan)

^b KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

Author keywords

Acetogenin; Antitumor; Asymmetric Synthesis; Polyketide; THF Ring

Indexed keywords

EID: 75849119298     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-09-11741     Document Type: Article

References (27)

1. For recent reviews, see. Makabe H., Konno H., and Miyoshi H. Curr. Drug. Discovery Technol. 5 (2008) 213
2. Makabe H. Biosci. Biotechnol. Biochem. 71 (2007) 2367
3. McLaughlin J.L. J. Nat. Prod. 71 (2008) 1311
4. Bermejo A., Figadère B., Zafra-Polo M.-C., Barrachina I., Estoneroll E., and Cortes D. Nat. Prod. Rep. 22 (2005) 269
5. Recent synthesis of annonaceous acetogenins, for recent review. Li N., Shi Z., Tang Y., Chen J., and Li X. Beilstein J. Org. Chem. 4 No. 48 (2008). http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-4-48
6. For recent synthesis. Morris C.L., Hu Y., Head G.D., Brown L.J., Whittingham W.G., and Brown R.C.D. J. Org. Chem. 74 (2009) 981
7. Griggs N.D., and Phillips A.J. Org. Lett. 10 (2008) 4955
8. Takahashi S., Hongo Y., Tsukagoshi Y., and Koshino H. Org. Lett. 10 (2008) 4223
9. Furuhata S., Hattori Y., Okajima M., Konno H., Abe M., Miyoshi H., Goto T., and Makabe H. Tetrahedron 64 (2008) 7695
10. Huh C.W., and Roush W.R. Org. Lett. 10 (2008) 3371
11. Hattori Y., Furuhata S., Okajima M., Konno H., Abe M., Miyoshi H., Goto T., and Makabe H. Org. Lett. 10 (2008) 717
12. Myint S.H., Cortes D., Laurens A., Hocquemiller R., Leboeuf M., Cavé A., Cotte J., and Quero A.-M. Phytochemistry 30 (1991) 3335
13. Gleye C., Duret P., Laurens A., Hocquemiller R., and Cavé A. J. Nat. Prod. 61 (1998) 576
14. Synthesis of solamin. Sinha S.C., and Keinan E. J. Am. Chem. Soc. 115 (1993) 4891
15. Trost B.M., and Shi Z. J. Am. Chem. Soc. 116 (1994) 7459
16. Makabe H., Tanaka A., and Oritani T. J. Chem. Soc., Perkin Trans. 1 (1994) 1975
17. Kuriyama W., Ishigami K., and Kitahara T. Heterocycles 50 (1999) 981
18. Raghavan S., Subramanian S.G., and Tony K.A. Tetrahedron Lett. 49 (2008) 1601
19. Synthesis of cis-solamin. Makabe H., Hattori Y., Tanaka A., and Oritani T. Org. Lett. 4 (2002) 1083
20. Makabe H., Hattori Y., Kimura Y., Konno H., Abe M., Miyoshi H., Tanaka A., and Oritani T. Tetrahedron 60 (2004) 10651
21. Cecil A.R.L., and Brown R.C.D. Org. Lett. 4 (2002) 3715
22. Cecil A.R.L., Hu Y., Vicent M.J., Duncan R., and Brown R.C.D. J. Org. Chem. 69 (2004) 3368
23. Göksel H., and Stark C.B. Org. Lett. 8 (2006) 3433
24. Konno H., Okuno Y., Makabe H., Nosaka K., Onishi A., Abe Y., Sugimoto A., and Akaji K. Tetrahedron Lett. 49 (2008) 782
25. Makabe H., Miyawaki A., Takahashi R., Hattori Y., Konno H., Abe M., and Miyoshi H. Tetrahedron Lett. 45 (2004) 973
26. Hattori Y., Kimura Y., Moroda A., Konno H., Abe M., Miyoshi H., Goto T., and Makabe H. Chem. Asian J. 1 (2006) 894
27. White J.D., Somers T.C., and Reddy G.N. J. Org. Chem. 57 (1992) 4991