Total synthesis of (±)-camphorataimides and (±)-himanimides by NaBH4/Ni(OAc)2 or Zn/AcOH stereoselective reduction

Tetrahedron

Volumn 64, Issue 19, 2008, Pages 4347-4353

  Cheng, Chia Fu ^a   Lai, Zhen Chang ^a   Lee, Yean Jang ^a  

^a NATIONAL CHANGHUA UNIVERSITY OF EDUCATION   (Taiwan)

Author keywords

Antrodia camphorate; Himanimides; NaBH4 Ni(OAc)2; Stereoselective reduction; Zn AcOH

Indexed keywords

1 HYDROXY 3 BENZYL 4 [4 (3 METHYL 2 BUTENYLOXY)PHENYL] 1H PYRROL 2,5 DIONE; 1 HYDROXY 3 BENZYL 4 [4 (3 METHYL 2 BUTENYLOXY)PHENYL]PYRROLIDINE 2,5 DIONE; 1 HYDROXY 3 ISOBUTYL 4 [4 (3 METHYL 2 BUTENYLOXY)PHENYL] 1H PYRROL 2,5 DIONE; 1 HYDROXY 3 ISOBUTYL 4 [4 (3 METHYL 2 BUTENYLOXY)PHENYL]PYRROLIDINE 2,5 DIONE; 3 BENZYL 4 [4 (3 METHYL 2 BUTENYLOXY)PHENYL]FURAN 2,5 DIONE; 3 ISOBUTYL 4 [4 (3 METHYL 2 BUTENYLOXY)PHENYL] 1H PYRROL 2,5 DIONE; 3 ISOBUTYL 4 [4 (3 METHYL 2 BUTENYLOXY)PHENYL]FURAN 2,5 DIONE; ACETIC ACID DERIVATIVE; ACETYL HYDROXIDE; CAMPHORATAIMIDE DERIVATIVE; CHINESE DRUG; HIMANIMIDE DERIVATIVE; IMIDE; MALEIC ANHYDRIDE; NATURAL PRODUCT; SODIUM BOROHYDRIDE; SUCCINIC ANHYDRIDE; UNCLASSIFIED DRUG;

ANTRODIA CAMPHORATE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHINESE MEDICINE; DRUG ISOLATION; DRUG STRUCTURE; MYCELIUM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUZUKI REACTION;

ANTRODIA;

EID: 41549140415     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.077     Document Type: Article

References (30)

1. Adlington R.M., Baldwin J.E., Cox R.J., and Pritchard G.J. Synlett (2002) 820 and references therein
2. Nakamura N., Hirakawa A., Gao J.J., Kakuda H., Shiro M., Komatsu Y., Sheu C.C., and Hattori M. J. Nat. Prod. 67 (2004) 46
3. Tsai Z.T., and Liaw S.L. The Use and the Effect of Ganoderma (1982), Sheng-Yun, Taichung, Taiwan p 116
4. Tseng T.H., Tsheng Y.M., Lee Y.J., and Hsu H.L. J. Chin. Chem. Soc. 47 (2000) 1165
5. Lin S.Y., Chen C.L., and Lee Y.J. J. Org. Chem. 68 (2003) 2968
6. Stille J.K. Angew. Chem., Int. Ed. Engl. 25 (1986) 508
7. Stille J.K., and Groh B.L. J. Am. Chem. Soc. 109 (1987) 813
8. Echavarren A.M., and Stille J.K. J. Am. Chem. Soc. 109 (1987) 5478
9. Baag M.M., and Argade N.P. Synthesis (2006) 1005
10. Stewart S.G., Polomska M.E., and Lim R.W. Tetrahedron Lett. 48 (2007) 2241
11. Bernard A.M., Cocco M.T., Onnis V., and Piras P.P. Synthesis 3 (1998) 256
12. Kelly T.R., Li Q., and Bhushan V. Tetrahedron Lett. 31 (1990) 161
13. Kelly T.R., and Jagoe C.T. Tetrahedron Lett. 32 (1991) 4263
14. Kelly T.R., and Lang F. Tetrahedron Lett. 36 (1995) 5319
15. Kelly T.R., and Lang F. J. Org. Chem. 61 (1996) 4623
16. Kelly T.R., Xu W., Ma Z., Li Q., and Bhushan V. J. Am. Chem. Soc. 115 (1993) 5843
17. Kelly T.R., Lee Y.J., and Mears R.J. J. Org. Chem. 62 (1997) 2774
18. Lutz R.E. J. Am. Chem. Soc. 52 (1930) 3423
19. Brown J.P. Chem. Abstr. 65 (1966) 2131a
20. Shoppee C.W., and Wu W.Y. Aust. J. Chem. 40 (1987) 1137
21. Horowska B., Mazerska Z., Ledochowski A., Cristalli G., Franchetti P., and Martelli S. Eur. J. Med. Chem. Chim. Ther. 23 (1988) 91
22. Choi D.S., Huang S., Huang M., Barnard T.S., Adams R.D., Seminario J.M., and Tour J.M. J. Org. Chem. 63 (1998) 2646
23. Carman R.M., Derbyshire R.P.C., Hansford K.A., Kadirverlaj R., and Robinson W.T. Aust. J. Chem. 54 (2001) 117
24. Dubernet M., Caubert V., Guillard J., and Viaud-Massuard M.-C. Tetrahedron 61 (2005) 4585
25. Gemal A.L., and Luche J.L. J. Am. Chem. Soc. 103 (1981) 5454
26. Comins D.L., Brooks C.A., and Ingalls C.L. J. Org. Chem. 66 (2001) 2181 and references therein
27. Selles P. Org. Lett. 7 (2005) 605
28. Aqueveque P., Anke T., and Sterner O. Z. Naturforsch. 57c (2002) 257
29. Autoclave, a PTFE-lined vessel No. 4749, was purchased from Parr Instrument Company, USA.
30. Joyce R.P., Gainor J.A., and Weinreb S.M. J. Org. Chem. 52 (1987) 1177