Atroposelective heck macrocyclization: Enantioselective synthesis of bis(bibenzylic) natural products

Organic Letters

Volumn 14, Issue 17, 2012, Pages 4548-4551

  Groh, Matthias ^a   Meidlinger, Daniel ^a   Bringmann, Gerhard ^b   Speicher, Andreas ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIBENZYL DERIVATIVE; BINAP, 2 NAPHTHOL; BINAP, 2-NAPHTHOL; BIOLOGICAL PRODUCT; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

BIBENZYLS; BIOLOGICAL AGENTS; CYCLIZATION; MOLECULAR STRUCTURE; NAPHTHALENES; STEREOISOMERISM;

EID: 84866039856     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302132s     Document Type: Article

References (25)

1. Asakawa, Y. In Progress in the Chemistry of Organic Natural Products; Herz, E., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.; Springer: Wien-New York, 1995, p 5.
2. Friederich, S.; Rueffer, M.; Asakawa, Y.; Zenk, M. H. Phytochemistry 1999, 52, 1195-1202
3. Asakawa, Y.; Toyota, M.; Tori, M.; Hashimoto, T. Spectroscopy 2000, 14, 149-175
4. Asakawa, Y.; Ludwiczuk, A.; Nagashima, F.; Toyota, M.; Hashimoto, T.; Tori, M.; Fukuyama, Y.; Harinantenaina, L. Heterocycles 2009, 77, 99-150
5. Hashimoto, T.; Kanayama, S.; Kan, Y.; Tori, M.; Asakawa, Y. Chem. Lett. 1996, 741-742
6. Keserü, G. M.; Kolossváry, I.; Nógrádi, M. J. Mol. Struct. 1995, 356, 143-148
7. Hashimoto, T.; Irita, H.; Takaoka, S.; Tanaka, M.; Asakawa, Y. Tetrahedron 2000, 56, 3153-3159
8. Toyota, M.; Yoshida, T.; Kan, Y.; Takaoka, S.; Asakawa, Y. Tetrahedron Lett. 1996, 37, 4745-4748
9. Scher, J. M.; Zapp, J.; Becker, H.; Kather, N.; Kolz, J.; Speicher, A.; Dreyer, M.; Maksimenka, K.; Bringmann, G. Tetrahedron 2004, 60, 9877-9881
10. Bringmann, G.; Mühlbacher, J.; Reichert, M.; Dreyer, M.; Kolz, J.; Speicher, A. J. Am. Chem. Soc. 2004, 126, 9283-9290
11. Harrowven, D. C.; Kostiuk, S. L. Nat. Prod. Rep. 2012, 29, 223-242
12. Eicher, T.; Fey, S.; Puhl, W.; Buchel, E.; Speicher, A. Eur. J. Org. Chem. 1998, 877-888
13. Speicher, A.; Kolz, J.; Sambanje, R. P. Synthesis 2002, 2503-2512
14. Esumi, T.; Wada, M.; Mizushima, E.; Sato, N.; Kodama, M.; Asakawa, Y.; Fukuyama, Y. Tetrahedron Lett. 2004, 45, 6941-6945
15. Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384-5427
16. Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051-12052
17. Oestreich, M., Ed. The Mizoroki-Heck Reaction; Wiley-VCH: Weinheim, 2009.
18. Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Stang, P. J.; Diederick, F., Eds.; VCH: Weinheim: 1998; pp 231-269.
19. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. 1994, 33, 2379-2411
20. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739
21. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846-5848
22. Speicher, A.; Backes, T.; Hesidens, K.; Kolz, J. Beilstein J. Org. Chem. 2009, 5, No. 71.
23. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6949-6951
24. Alcazar-Roman, L. M.; Hartwig, J. F.; Rheingold, A. L.; Liable-Sands, L. M.; Guzei, I. A. J. Am. Chem. Soc. 2000, 122, 4618-4630
25. Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598-1603