Total synthesis of the putative structure of the novel triquinane based sesquiterpenoid natural product dichomitol

Tetrahedron Letters

Volumn 47, Issue 47, 2006, Pages 8355-8360

  Mehta, Goverdhan ^a   Pallavi, Kotapalli ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DICHOMITOL; NATURAL PRODUCT; SESQUITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; FERMENTATION; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

DICHOMITUS SQUALENS;

EID: 33750094698     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.084     Document Type: Article

References (33)

1. For a recent entrant to the triquinane based natural products family, see:. Roncal T., Cordobes S., Ugalde U., He Y., and Sterner O. Tetrahedron Lett. 43 (2002) 6799-6802
2. Recent reviews:. Mehta G., and Srikrishna A. Chem. Rev. 97 (1997) 671-719
3. Singh V., and Thomas B. Tetrahedron 54 (1998) 3647-3692
4. Huang Z., Dan Y., Huang Y., Lin L., Li T., Ye W., and Wei X. J. Nat. Prod. 67 (2004) 2121-2123
5. For some of the recent accomplishments in the area of linear triquinane natural product syntheses from other groups, see:. Banwell M.G., Edwards A.J., Harfoot G.J., and Jolliffe K.A. Tetrahedron 60 (2004) 535-547
6. Wang J.C., and Krische M.J. Angew. Chem., Int. Ed. 42 (2003) 5855-5857
7. Singh V., Vedantham P., and Sahu P.K. Tetrahedron Lett. 43 (2002) 519-522
8. Mukai C., Kobayashi M., Kim I.J., and Hanaoka M. Tetrahedron 58 (2002) 5225-5230
9. Shindo M., Sato Y., and Shishido K. Tetrahedron Lett. 43 (2002) 5039-5041
10. Harrowven D.C., Lucas M.C., and Howes P.D. Tetrahedron 57 (2001) 9157-9162
11. Mehta G., and Reddy A.V. J. Chem. Soc., Chem. Commun. (1981) 756-757
12. Mehta G., Reddy A.V., Murty A.N., and Reddy D.S. J. Chem. Soc., Chem. Commun. (1982) 540-541
13. Mehta G., Reddy D.S., and Murty A.N. J. Chem. Soc., Chem. Commun. (1983) 824-825
14. Mehta G., Murthy A.N., Reddy D.S., and Reddy A.V. J. Am. Chem. Soc. 108 (1986) 3443-3452
15. Mehta G., and Karra S.R. J. Chem. Soc., Chem. Commun. (1991) 1367-1368
16. Mehta G., and Umarye J.D. Tetrahedron Lett. 42 (2001) 1991-1993
17. Mehta G., Murthy A.S.K., and Umarye J.D. Tetrahedron Lett. 43 (2002) 8301-8305
18. Mehta G., and Murthy A.S.K. Tetrahedron Lett. 44 (2003) 5243-5246
19. Mehta G., and Sreenivas K. Chem. Commun. (2001) 1892-1893
20. Mehta G., and Sreenivas K. Tetrahedron Lett. 43 (2002) 703-706
21. 3): δ 4.48 (br s, 1H), 4.40 (d, J = 15.4 Hz, 1H), 4.15 (d, J = 15.4 Hz, 1H), 3.49 (s, 2H), 2.81-2.75 (m, 1H), 2.66-2.60 (m, 1H), 2.57 (q, J = 9.1 Hz, 1H), 2.29 (q, J = 7.7 Hz, 1H), 1.78 (ddd, J = 12.6, 8.4, 1.4 Hz, 1H), 1.75-1.70 (m, 2H)
22. Ito Y., Hirao T., and Saegusa T. J. Org. Chem. 43 (1978) 1011-1013
23. Horiguchi Y., Matsuzawa S., Nakamura E., and Kuwajima I. Tetrahedron Lett. 27 (1986) 4025-4028
24. Nakamura E., Matsuzawa S., Horiguchi Y., and Kuwajima I. Tetrahedron Lett. 27 (1986) 4029-4032
25. Kende A.S., Roth B., and Sanfilippo P.J. J. Am. Chem. Soc. 104 (1982) 1784-1785
26. o) and 0.1611 for all 11330 data. wR2 = 0.2555, GOF = 1.048, Restrained GOF = 1.048 for all data. CCDC 617731.
27. Tsuji J. Synthesis (1984) 369-384
28. Ranieri R.L., and Calton G.J. Tetrahedron Lett. 19 (1978) 499-502
29. Calton G.J., Ranieri R.L., and Espenshade M.A. J. Antibiot. 31 (1978) 38-45
30. Nakagawa M., Hirota A., Sakai H., and Isogai A. J. Antibiot. 35 (1982) 778-782
31. Frigerio M., and Santagostino M. Tetrahedron Lett. 35 (1994) 8019-8022
32. 3, DCM, 0 °C, 30 min., 95%.
33. Martin J.C., and Arhart R.J. J. Am. Chem. Soc. 93 (1971) 4327-4329