Synthesis of 2(3)-8(9)-bisanhydrolactarorufin A

Tetrahedron

Volumn 53, Issue 40, 1997, Pages 13703-13708

  Wockenfuß, Bernd ^a   Wolff, Christian ^a   Tochtermann, Werner ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

Hydroazulenes; Lactarane sesquiterpenoids; Ring enlargement; Ruthenium tetroxide

Indexed keywords

SESQUITERPENOID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030812785     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00888-0     Document Type: Article

References (23)

1. Review: Ayer, W. A.; Browne, L. M. Tetrahedron 1981, 37, 2199-2248.
2. Recent examples: a) Sterner, O; Carter, R. E.; Nilsson, L. Mutat. Res. 1987, 188, 169-174.
3. b) Anke, H.; Sterner, O. Planta. Med. 1991, 57, 344-346.
4. c) Bocchio, F.; Kalf-Hansen, S.; Dekermendjian, K.; Sterner, O.; Witt, R. Tetrahedron Lett. 1992, 33, 6867-687.
5. d) Daniewski, W. M.; Gumulka, M; Przesmycka, D.; Ptaszyńska, K.; Bloszyk, E.; Drożdż, B. Phytochemistry 1995, 38, 1161-1168.
6. e) Wunder, A.; Anke, T.; Klostermeyer, D.; Steglich, W. Z. Naturforsch. 1996, 51c, 493-499.
7. a) Tochtermann, W.; Bruhn, S.; Meints, M.; Wolff, C. Tetrahedron 1994, 50, 9657-9670.
8. b) Tochtermann, W., Bruhn, S.; Meints, M.; Wolff, C.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Tetrahedron 1995, 51, 1623-1630.
9. For earlier lactarane syntheses see ref 1, 3 and a ) Price, M. E.; Schore, N. E. Tetrahedron Lett. 1989, 30, 5865-5868.
10. b) Molander, G.; Carey, J. S. J. Org. Chem. 1995, 60, 4845-4849.
11. c) Ogino, T.; Kurihara, C.; Baba, Y.; Kanematsu, K. J. Chem. Soc. Chem. Commun. 1994, 1979-1980.
12. d) Seki, M; Sakamoto, T; Suemune, H; Kanematsu, K. J. Chem. Soc., Perkin Trans 1 1997, 1707-1714 and references therein.
13. The numbering of the lactarane skeleton according to ref. 1 and 6 is used for 8. 3-7 are numbered as hydroazulenes.
14. a) Daniewski, W. M.; Gumulka, M.; Skibicki, P.; Krajewski, J.; Gluziński, P. Phytochemistry 1991, 30, 1326-1328.
15. b) Daniewski, W. M.; Gumulka, M.; Ptaszyńska, K.; Skibicki, P.; Jacobsson, U.; Norin, T. Phytochemistry 1992, 31, 3933-3936.
16. For details see: Bruhn, S. Dissertation, University of Kiel, 1995.
17. Guindon, Y.; Therien, M.; Girard, Y.; Yoakim, Y. J. Org. Chem. 1987, 52, 1680-1686.
18. For details see: Wockenfuß, B. Dissertation, University of Kiel, 1997.
19. a) Nysted, L. N.; U. S. Patent 3865848 (1975); Chem. Abstr. 1975, 83, 10406q.
20. b) Nysted, L. N.; U. S. Patent 3960904 (1976); Chem. Abstr. 1976, 85, 94618n.
21. c) Aldrichimica Acta 1993, 26, 14.
22. According to a CAS Online searching on March 14, 1997 no total synthesis of 8 was reported earlier.
23. Bailey, D. M.; Johnson, R. E. J. Org. Chem. 1970, 35, 3574-3576.