Synthesis of (+)-myrtopsine, (+)-7,8-dimethoxymyrtopsine, and related 2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methyl-ethyl)benzofuran natural products

Heterocycles

Volumn 70, Issue , 2006, Pages 279-294

  Snider, Barry B ^a   Wu, Xiaoxing ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947666148     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-06-s(w)20     Document Type: Article

References (37)

1. Zou Y., Lobera M., and Snider B.B. J. Org. Chem. 70 (2005) 1761
2. Knochel P., Dohle W., Gommermann N., Kneisel F.F., Kopp F., Kom T., Sapountzis I., and Vu V.A. Angew. Chem. Int. Ed. 42 (2003) 4302
3. Varchi G., Kofink C., Lindsay D.M., Ricci A., and Knochel P. Chem. Commun. (2003) 396
4. Hifnawy M.S., Vaquette J., Sévenet T., Pousset J.L., and Cavé A. Planta Med. 29 (1976) 346
5. Hifnawy M.S., Vaquette J., Sévenet T., Pousset J.L., and Cavé A. Phytochemistry 16 (1977) 1035
6. Akhmedzhanova V.I., and Bessonova I.A. Khim. Prir. Soedin. (1981) 613
7. Akhmedzhanova V.I., and Bessonova I.A. Chem. Nat. Comp. (1981) 447
8. Akhmedzhanova V.I., and Bessonova I.A. Chem. Abstr. 96 (1982) 31670e
9. Muyard F., Bevalot F., Laude B., and Vaquette J. Phytochemistry 31 (1992) 1087
10. Chen I.-S., Chen H.-F., Cheng M.-J., Chang Y.-L., Teng C.-M., Ishikawa T., Chen J.-J., and Tsai I.-L. J. Nat. Prod. 64 (2001) 1143
11. Marschall H., Penninger J., and Weyerstahl P. Liebigs Ann. Chem. (1982) 49
12. Bar G., Parsons A.F., and Thomas C.B. Tetrahedron 57 (2001) 4719
13. Glover B., Harvey K.A., Liu B., Sharp M.J., and Tymoschenko M.F. Org. Lett. 5 (2003) 301
14. Chen I.-L., Chen Y.-L., and Tzeng C.-C. Helv. Chim. Acta 85 (2002) 2214
15. Ziegler E., Salvador R., and Kappe Th. Monatsh. Chem. 94 (1963) 941
16. Gaston J.L., Greer R.J., and Grundon M.F. J. Chem. Res., Miniprint (1985) 1877
17. Reisch J., and Bathe A. Liebigs Ann. Chem. (1988) 69
18. Chen Y.-L., Hung H.-M., Lu C.-M., Li K.-C., and Tzeng C.-C. Bioorg. Med. Chem. 12 (2004) 6539
19. Prepared by Sharpless asymmetric epoxidation of 3-methyl-2-buten-l-ol using (L)-(+)-diisopropyl tartrate to give the (S)-epoxy alcohol, which was converted to (R)-1 by a Swern oxidation:. Gao Y., Hanson R.M., Klunder J.M., Ko S.Y., Masamune H., and Sharpless K.B. J. Am. Chem. Soc. 109 (1987) 5765
20. Evans D.A., and Williams J.M. Tetrahedron 29 (1988) 5065
21. Beak P., Woods T.S., and Mueller D.S. Tetrahedron 28 (1972) 5507
22. Arndt F., Ergener L., and Kutlu O. Chem. Ber. 86 (1953) 951
23. Tokay N., and Ögretir C. J. Mol. Struct. 594 (2002) 185
24. Brown N.M.D., Grundon M.F., Harrison D.M., and Surgenor S.A. Tetrahedron 36 (1980) 3579
25. Pusset J., Lopez J.L., Pais M., Al Neirabeyeh M., and Veillon J.-M. Planta Med. 57 (1991) 153
26. Purchased from Apin Chemicals LTD.
27. Tagawa Y., Kawaoka T., and Goto Y. J. Heterocycl. Chem. 34 (1997) 1677
28. Boyd D.R., Sharma N.D., Boyle R., Evans T.A., Malone J.F., McCombe K.M., Dalton H., and Chima J. J. Chem. Soc., Perkin Trans. 1 (1996) 1757
29. Ito C., Itoigawa M., Furukawa A., Hirano T., Murata T., Kaneda N., Hisada Y., Okuda K., and Furukawa H. J. Nat. Prod. 67 (2004) 1800
30. Lee Y.R., Choi J.H., Trinh D.T.L., and Kim N.W. Synthesis (2005) 3026
31. Friedrich U., Siems K., Solis P.N., Gupta M.P., and Jenett-Siems K. Pharmazie 60 (2005) 455
32. Krasovskiy A., and Knochel P. Angew. Chem., Int. Ed. 43 (2004) 3333
33. Kopp F., Krasovskiy A., and Knochel P. Chem. Commun. (2004) 2288
34. Talley J.J. Synthesis (1983) 845
35. Rossiter B.E., Verhoeven T.R., and Sharpless K.B. Tetrahedron Lett. (1979) 4733
36. Adam W., and Wirth T. Acc. Chem. Res. 32 (1999) 703
37. Private communication, Dr. K. Jenett-Siems, Feb. 16, 2006.