Total syntheses of (+)-chloropuupehenone and (+)-chloropuupehenol and their analogues and evaluation of their bioactivities

Journal of Organic Chemistry

Volumn 69, Issue 18, 2004, Pages 6065-6078

  Hua, Duy H ^a   Huang, Xiaodong ^a   Chen, Yi ^a   Battina, Srinivas K ^a   Tamura, Masafumi ^a   Noh, Sang K ^a,c   Koo, Sung I ^a,d   Namatame, Ichiji ^b   Tomoda, Hiroshi ^b   Perchellet, Elisabeth M ^a   Perchellet, Jean Pierre ^a  

^a KANSAS STATE UNIVERSITY   (United States)

^b KITASATO UNIVERSITY   (Japan)

^c Changwon National University   (South Korea)

^d UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INTESTINAL ABSORPTION; ONE-POT CONDENSATION; RING-CLOSURE REACTIONS; STEREOSELECTIVE SYNTHESIS;

ABSORPTION; CHOLESTEROL; CONDENSATION; ESTERS; PROTEINS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

POLYCYCLIC AROMATIC HYDROCARBONS;

ALBICANAL; ALBICANOL; ALPHA TOCOPHEROL; CARBON 14; CHLOROPUUPEHENOL; CHLOROPUUPEHENONE; CHOLESTEROL; CHOLESTEROL ESTER TRANSFER PROTEIN; DRIMANE 8ALPHA,11 DIOL; DRIMENOL; OLEIC ACID; PYRAN DERIVATIVE; SESQUITERPENE; TAURODIHYDROFUSIDATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHOLESTEROL TRANSPORT; FATTY ACID ANALYSIS; ISOTOPE LABELING; MALE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STEREOCHEMISTRY; SYNTHESIS;

ANIMALS; CARRIER PROTEINS; CHOLESTEROL ESTER TRANSFER PROTEINS; CYCLIZATION; GLYCOPROTEINS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INHIBITORY CONCENTRATION 50; LEUKEMIA L1210; MOLECULAR STRUCTURE; PYRANS; RATS; SESQUITERPENES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4344600961     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0491399     Document Type: Article

References (53)

1. Hua, D. H.; Chen, Y.; Sin, H.-S.; Maroto, M. J.; Robinson, P. D.; Newell, S. W.; Perchellet, E. M.; Ladesich, J. B.; Freeman, J. A.; Perchellet, J.-P.; Chiang, P. K. J. Org. Chem. 1997, 62, 6888-6896.
2. Hua, D. H.; Huang, X.; Tamura, M.; Chen, Y.; Woltkamp, M.; Jin, L.-W.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Tomoda, H. Tetrahedron 2003, 59, 4795-4803.
3. Isolation of chloropuupehenone, bromopuupehenone, and puupehenone: (a) Ravi, B. N.; Perzanowski, H. P.; Ross, R. A.; Erdman, T. R.; Scheuer, P. J. Pure Appl. Chem. 1979, 51, 1893-1900.
4. (b) Amade, P.; Chevelot, L.; Perzanowski, H. P.; Scheuer, P. J. Helv. Chim. Acta 1983, 66, 1672-1675.
5. (c) Hamann, M. T.; Scheuer, P. J. Tetrahedron Lett. 1991, 32, 5671-5672.
6. Isolation of chloropuupehenone and its metabolites: (d) Hamann, M. T.; Scheuer, P. J. J. Org. Chem. 1993, 58, 6565-6569.
7. Puupehenone-related metabolites: (e) Nasu, S. S.; Yeung, B. K. S.; Hamann, M. T.; Scheuer, P. J.; Kelly-Borges, M.; Goins, K. J. Org. Chem. 1995, 60, 7290-7292.
8. Absolute stereochemistry of puupehenone and related metabolites: (f) Urban, S.; Capon, R. J. J. Nat. Prod. 1996, 59, 900-901.
9. CETP inhibition: (a) Coval, S. J.; Conover, M. A.; Mierzwa, R.; King, A.; Puar, M. S.; Phife, D. W.; Pai, J.-K.; Burrier, R. E.; Ahn, H.-S.; Boykow, G. C.; Patel, M.; Pomponi, S. A. Bioorg. Med. Chem. Lett. 1995, 5, 605-610.
10. Antimicrobial and cytotoxic activity of puupehenone and chloropuupehenone: (b) Popov, A. M.; Stekhova, S. I.; Utkina, N. K.; Rebachuk, N. M. Pharm. Chem. J. 1999, 33, 71-73.
11. Antimalarial activity: (c) El Sayed, K. A.; Dunbar, D. C.; Goins, D. K.; Cordova, C. R.; Perry, T. L.; Wesson, K. J.; Sanders, S. C.; Janus, S. A.; Hamann, M. T. J. Nat. Toxins 1996, 5, 261-285.
12. Antituberculosis: (d) El Sayed, K. A.; Bartyzel, P.; Shen, X. D.; Perry, T. L.; Zjawiony, J. K.; Hamann, M. T. Tetrahedron 2000, 56, 949-953.
13. For reviews of CETP and atherosclerosis: (a) Ross, R. Nature 1993, 362, 801-809.
14. (b) Tall, A. R. J. Lipid Res. 1993, 34, 1255-1274.
15. (c) Lagrost, L. Biochim. Biophys. Acta 1994, 1215, 209-236.
16. (d) Wang, J.; Qiang, H.; Zhang, C. D.; Zhuang, Y. Clin. Chim. Acta 2002, 322, 85-90.
17. Synthesis of puupehenone: (a) Trammell, G. I. Tetrahedron Lett. 1978, 18, 1525-1528.
18. (b) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328.
19. (c) Barrero, A. F.; Manzaneda, E. J. A.; Chahboun, R.; Cortes, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208.
20. (d) Quideau, S.; Lebon, M.; Lamidey, A.-M. Org. Lett. 2002, 4, 3975-3978.
21. Synthesis of 15-oxopuupehenonol: (e) Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Saez, B. Tetrahedron Lett. 1997, 38, 7249-7252.
22. Synthesis of 8-epipuupehenone: (f) Armstrong, V.; Barrero, A. F.; Alvarez-Manzaneda, E. J.; Cortes, M.; Sepulveda, B. J. Nat. Prod. 2003, 66, 1382-1383.
23. (a) Loest, H. B.; Noh, S. K.; Koo, S. I. J. Nutr. 2002, 132, 1282-1288.
24. For reviews: (b) Bays, H.; Stein, E. A. Expert Opin. Pharmacother. 2003, 4, 1901-1938.
25. (c) Wierzbicki, A. S. Expert Opin. Emerg. Drugs 2003, 8, 365-376.
26. (d) Curatolo, W. J.; Sutton, S. C.; Appel, L. E. PCT Int. Appl. 2003063868, 2003; 176 pp.
27. Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294.
28. (a) Barrero, A. F.; Manzaneda, E. A.; Chahboun, R. Tetrahedron Lett. 1997, 38, 8101-8104 and references therein.
29. (b) Barreoro, A. F.; Manzaneda, E. A.; Chahboun, R. Tetrahedron 1998, 54, 5635-5650.
30. (c) Chackalamannil, S.; Wang, Y.; Xia, Y.; Czarniecki, M. Tetrahedron Lett. 1995, 36, 5315-5318.
31. Vedejs, E.; Engler, D. A.; Telschow, J. E. J. Org. Chem. 1978, 43, 188-196.
32. Hann, R. M.; Spencer, G. C. J. Am. Chem. Soc. 1927, 49, 535-7.
33. Jong, T. T.; Williard, P. G.; Porwoll, J. P. J. Org. Chem. 1984, 49, 735-6.
34. Godfrey, I. M.; Sargent, M. V.; Elis, J. A. J. Chem. Soc., Perkin Trans. 1974, 1, 1353.
35. (a) Hlubucek, J. R.; Aasen, A. J.; Almqvist, S.-O.; Enzell, C. R. Acta Chem. Scand. B 1974, 28, 289-294.
36. (b) Kuchkova, K. I.; Chumakov, Y. M.; Simonov, Y. A.; Bocelli, G.; Panasenko, A. A.; Vlad, P. F. Synthesis 1997, 1045-1046,
37. (c) Shishido, K.; Omodani, T.; Shibuya, M, J. Chem. Soc., Perkin Trans. 1 1991, 2285-2287.
38. (a) Toshima, H.; Oikawa, H.; Toyomasu, T.; Sassa, T. Biosci. Biotechnol. Biochem. 2001, 65, 1244-1247.
39. (b) Poigny, S.; Huor, T.; Guyot, M.; Samadi, M. J. Org. Chem. 1999, 64, 9318-9320.
40. Isolation of (-)-albicanal and (+)-albicanol: (c) Toyota, M.; Ooiso, Y.; Kusuyama, T.; Asakawa, Y. Phytochemistry 1994, 35, 1263-1265.
41. (d) Weyerstahl, P.; Marschall, H.; Schneider, S. Flavour Fragrance J. 1995, 10, 179-185.
42. Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704-3706.
43. Tomoda, H.; Tabata, N.; Masuma, R.; Si, S.-Y.; Omura, S. J. Antibiot. 1998, 51, 618-623.
44. Tomoda, H.; Tabata, N.; Shinose, M.; Takahashi, Y.; Woodruff, H. B.; Omura, S. J. Antibiot. 1999, 52, 1101-1107.
45. Noh, S. K.; Koo, S. I.; Jiang, Y. Nutraceut. Food 2003, 8, 1-6.
46. Gutierrez, P. L. Front. Biosci. 2000, 5, D629-638; electronic publication.
47. For a review, see: Vilella, D.; Sanchez, M.; Platas, G.; Salazar, O.; Genilloud, O.; Royo, I.; Cascales, C.; Martin, I.; Diez, T.; Silverman, K. C.; Lingham, R. B.; Singh, S. B.; Jayasuriya, H.; Pelaez, F. J. Ind. Microbiol. Biotechnol. 2000, 25, 315-327.
48. Kaiser, C.; Colella, D. F.; Pavloff, A. M.; Wardell, J. R. J. J. Med. Chem. 1974, 17, 1071-1075.
49. (a) Tomoda, H.; Tabata, N.; Masuma, R.; Si, S.-Y.; Omura, S. J. Antibiot. 1998, 51, 618-623.
50. (b) Perchellet, E. M.; Ladesich, J. B.; Magill, M. J.; Chen, Y.; Hua, D. H.; Perchellet, J. P. Anti-Cancer Drugs 1999, 10, 489-504.
51. Reeves, P. G.; Nielsen, F. H.; Fahey, G. C., Jr. J. Nutr. 1993, 123, 1939-1951.
52. Reeves, P. G. In Trace Elements in Laboratory Rodents; Watson, R. R., Ed.; CRC Press: Boca Raton, FL, 1996; pp 3-37.
53. Koo, S. I.; Noh, S. K. J. Nutr. 2001, 131, 717-722.