First synthesis of mastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 483-486

  Bringmann, Gerhard ^a   Pabst, Thomas ^a   Rycroft, David S ^b   Connolly, Joseph D ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MASTIGOPHORENE A; MASTIGOPHORENE B; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; PLANT;

HERBERTUS ADUNCUS;

EID: 0033556227     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02487-3     Document Type: Article

References (15)

1. "Novel concepts in directed biaryl synthesis", part 76, for part 75 see Bringmann, G.; Saeb, W.; Rübenacker, M. Tetrahedron, in press.
2. Fukuyama, Y.; Asakawa, Y. J. Chem. Soc., Perkin Trans. I 1991, 2737-2741.
3. Toyota, M.; Koyama, H.; Asakawa, Y. Phytochemistry 1997, 46, 145-150.
4. Zinsmeister, H.D.; Becker, H.; Eicher, T. Angew. Chem. 1991, 103, 134-151; Angew. Chem. Int. Ed. Engl. 1991, 30, 130-147.
5. Zinsmeister, H.D.; Becker, H.; Eicher, T. Angew. Chem. 1991, 103, 134-151; Angew. Chem. Int. Ed. Engl. 1991, 30, 130-147.
6. Bringmann, G.; Pabst, T.; Busemann, S.; Peters, K.P.; Peters, E.-M. Tetrahedron 1998, 54, 1425-1438.
7. Correctly speaking, the biaryls 1 and 2 are not dimers, but dehydrodimers of the corresponding 'monomeric' phenolic compounds 3 and 4, respectively; for reasons of simplicity, the terms 'dimer' or 'dimerization' will, nonetheless, be used in this paper.
8. Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem. 1990, 102, 1006-1019; 977-991.
9. Bringmann, G.; Tasler, S. In Current Trends in Organic Synthesis; Scolastico, C.; Nicotra, F. Eds.; Plenum Publishing Corporation: New York 1999, in press.
10. Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M.R.; Gulakowski, R.J.; François, G. Tetrahedron 1998, 54, 497-512.
11. Buchanan, M.S.; Connolly, J.D.; Rycroft, D.S. Phytochemistry 1996, 43, 1245-1248.
12. 3), 6.65 (d, J = 0.6, 1H, Ar-H), 6.66 (d, J = 0.6, 1H, Ar-H).
13. Bringmann, G.; Schneider, S. Synthesis 1983, 139-141.
14. Armstrong, D. R.; Breckenbridge, R. J.; Cameron, C.; Nonhebel, D. C.; Pauson, P. L.; Perkins, P. G. Tetrahedron Lett. 1983, 24, 1071-1074.
15. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1996, 37, 1261-1264; a stereoselective approach has been presented as possible by the described pathway.