Isolation, structural elucidation, and synthesis of curcutetraol

European Journal of Organic Chemistry

Volumn , Issue 2, 2005, Pages 334-341

  Mülhaupt, Tanja ^a   Kaspar, Hannelore ^a   Otto, Sabine ^a   Reichert, Matthias ^b   Bringmann, Gerhard ^b   Lindel, Thomas ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Alcohols; Natural products; Stereochemical analysis; Terpenoids; Total synthesis

Indexed keywords

ALCOHOL; AMIDE; BENZYL ALCOHOL; CURCUDIOL; CURCUPHENOL; CURCUTETRAOL; CURCUTRIOLAMIDE; NATURAL PRODUCT; SESQUITERPENOID; SILICON DIOXIDE; TERPENOID; UNCLASSIFIED DRUG;

ARTICLE; BACTERIUM; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CIRCULAR DICHROISM; FUNGUS; MARINE ENVIRONMENT; NONHUMAN; PURIFICATION; QUANTUM CHEMISTRY; RACEMIZATION; SPONGE (PORIFERA); STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TOTAL SYNTHESIS;

EID: 12944320834     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400336     Document Type: Article

References (41)

1. [1a] I. Wagner-Döbler, W. Beil, S. Lang, M. Meiners, H. Laatsch, Adv. Biochem. Eng. Sci. 2002, 74, 207-238,
2. [1b] P. R. Jensen, W. Fenical, in Drugs from the Sea (Ed.: N. Fusetani). Karger, 2000. pp. 6-29.
3. V. K. Honwad, A. S. Rao, Tetrahedron 1965, 21, 2593-2604 and references cited therein.
4. P. W. Jeffs, L. T. Lytle, Lloydia 1974, 37, 315-317.
5. F. J. McEnroe, W. Fenical, Tetrahedron 1978, 4, 1661-1664.
6. [5a] A. E. Wright, S. A. Pomponi, O. J. McConnell, S. Kohmoto, P. J. McCarthy, J. Nat. Prod. 1987, 50, 976-978.
7. [5b] D. Taşdemir, T. S. Bugni, G. C. Mangalindan, G. P. Concepcion, M. K. Harper, C. M. Ireland, Turk. J. Chem. 2003, 27, 273-279.
8. N. Fusetani, M. Sugano, S. Matsunaga, K. Hashimoto, Experientia 1987, 43, 1234-1235.
9. M. S. Butler, R. J. Capon, R. Nadeson, A. A. Beveridge, J. Nat. Prod. 1991, 54, 619-623.
10. [8a] B. Harrison, P. Crews, J. Org. Chem. 1997, 62, 2646-2648.
11. [8b] C.-Y. Chen, Y.-C. Shen, Y.-J. Chen, J.-H. Sheu, C.-Y. Duh, J. Nat. Prod. 1999, 62, 573-576.
12. I. Kitagawa, N. Yoshioka, C. Kamba, M. Yoshikawa, Y. Hamamoto, Chem. Pharm. Bull. 1987, 35, 928-931.
13. [10a] B. W. Sullivan, D. J. Faulkner, K. T. Okamoto, M. H. M. Chen, J. Clardy, J. Org. Chem. 1986, 57, 5134-5136.
14. [10b] N. K. Gulavita, E. Dilip de Silva, M. R. Hagadone, P. Karuso, P. J. Scheuer, G. D. Van Duyne, J. Clardy, J. Org. Chem. 1986, 57, 5136-5139.
15. M. Nukina, Y. Sato, M. Ikeda, T. Sassa, Agric. Biol. Chem. 1981, 45, 789-790.
16. P. Henne, R. Thiericke, S. Grabley, K. Hütter, J. Wink, E. Jurkiewicz. A. Zeeck, Liebigs Ann. Chem. 1993, 565-571.
17. P. R. Vijayasarathy, R. B. Mane, R. G. S. Krishna, J. Chem. Soc., Perkin Trans. 1 1977, 34-36.
18. Retention times 18.3 min (Chiralpak AD-H, 250 × 4.6 mm; heptane/EtOH/MeOH, 5:1:1; flow rate 1 mL/min, 30 °C) and 10.0 min (Chiralcel OJ, 250 × 4.6 mm; heptane/EtOH/MeOH, 15:1:1; flow rate 1 mL/min, 30 °C).
19. G. M. Hanna, C. A. Lau-Cam, W. M. Plank, Pharmazie 1989, 44, 321-325.
20. D. Parker, Chem. Rev. 1991, 91, 1441-1457.
21. [17a] S. Porto, J. Duran, J. M. Seco, E. Quiñoa, R. Riguera, Org. Lett. 2003, 5, 2979-2982 and references cited therein.
22. For a rare example on tertiary alcohols, see: [17b] S. Izumi, H. Moriyoshi, T. Hirata, Bull. Chem. Soc. Jpn. 1994, 67, 2600-2602.
23. A. Archelas, R. Furstoss, J. Org. Chem. 1999, 64, 6112-6114.
24. D. Q. Yu, F. Z. Xie, R. Y. Chen, Y. H. Huang, Chin. Chem. Lett. 1996, 7, 721-722.
25. H. Mizuno, S. Yamada. Chem. Pharm. Bull. 1975, 23, 527-537.
26. G. Casiraghi, F. Bigi, G. Casnati, G. Sartori, P. Soncini, G. G. Fava, M. F. Belicchi, J. Org. Chem. 1988, 53, 1779-1785.
27. G. Bringmann, S. Busemann, in Natural Product Analysis (Eds.: P. Schreier, M. Herderich, H. U. Humpf, W. Schwab), Vieweg, Wiesbaden, 1998, pp. 195-212.
28. G. Bringmann, J. Mühlbacher, C. Repges, J. Fleischhauer, J. Comput. Chem. 2001, 22, 1273-1278.
29. G. Bringmann, S. Tasler, H. Endress, J. Kraus, K. Messer, M. Wohlfarth, W. Lobin, J. Am. Chem. Soc. 2001, 123, 2703-2711.
30. G. Bringmann, M. Dreyer, J. H. Faber, P. W. Dalsgaard, D. Staerk, J. W. Jaroszewski, H. Ndangalasi, F. Mbago, R. Brun, M. Reichert, K. Maksimenka, S. B. Christensen, J. Nat. Prod. 2003, 66, 1159-1165.
31. SYBYL; Tripos Associates: 1699 Hanley Road, Suite 303, St. Louis. MO 63144.
32. N. L. Allinger, Y. H. Yuh, J.-H. Lu, J. Am. Chem. Soc. 1989, 111, 8551-8566.
33. J. Del Bene, H. H. Jaffé, J. Chem. Phys. 1968, 48, 1807-1813.
34. Interestingly, the CD spectrum calculated for (R)-1 was nearly opposite to the experimental one obtained for the secondary alcohol (R)- methylphenylcarbinol (L. Verbit, J. Am. Chem. Soc. 1965, 87, 1617-1619). That this seemingly opposite CD behavior of the two, yet only at first glance similar, compounds is also to be expected, was again demonstrated by quantum chemical CD calculations of (A)-methylphenylcarbinol, which resulted in a curve that was in a nearly perfect agreement with the experimental one for R, showing once again the reliability of quantum chemical calculations.
35. M. J. S. Dewar, E. G. Zoebisch, E. Healy, J. J. P. Steward, J. Am. Chem. Soc. 1985, 107, 3902-3909.
36. W. Weber, W. Thiel, Theor. Chem. Acc. 2000, 103, 495-506.
37. V. Ankala, G. Fenteany, Tetrahedron Lett. 2002, 43, 4729-4732.
38. F. Bohlmann, U. Niedballa, J. Schulz, Chem. Ber. 1969, 102, 864-871.
39. G. Rauhut, J. Chandrasekhar, A. Alex, B. Beck, W. Sauer, T. Clark, VAMP 6.5; Oxford Molecular Ltd.: Medewar Centre, Oxford Science Park, Sandford-on-Thames, Oxford. OX4 4GA, UK.
40. J. W. Downing, Software Package BDZDO/MCDSPD, Department of Chemistry and Biochemistry, University of Colorado: Boulder, USA; modified by J. Fleischhauer, W. Schleker, B. Kramer, ported to Linux by K.-P. Gulden.
41. W. Thiel, Software Package MNDO99, Version 6.0, Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim, Germany.