A tether controlled exo-selective trans-annular Diels - Alder (TADA) reaction

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3849-3851

  Felzmann, Wolfgang ^a   Arion, Vladimir B ^b   Mieusset, Jean Luc ^a   Mulzer, Johann ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BRANIMYCIN; MACROLIDE;

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

ANTI-BACTERIAL AGENTS; CYCLIZATION; MACROLIDES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33748629930     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061510m     Document Type: Article

References (31)

1. For reviews on TADA reactions, see: (a) Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779 and references therein.
2. (b) Marsault, E.i Toro, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243 and references therein.
3. An example showing low selectivity has been reported: Suzuki, T.; Usui, K.; Miyake, Y.; Namikoshi, M.; Nakada, M. Org. Lett. 2004, 6, 553.
4. Enev, V. S.; Drescher, M.; Kaehlig, H.; Mulzer, J. Synlett 2005, 14, 2227.
5. Speitling, M. Ph.D. Thesis, Universität Göttingen, 1998.
6. (a) For a review see: Kallmerten, J. Studies in Natural Products Chemistry; Elsevier: Amsterdam, The Netherlands, 1995; Vol. 17, pp 283-310 and cited literature.
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8. (c) See also: Tone, J.; Shibakawa, R.; Maeda, H.; Yamauchi, Y.; Niki, K.; Saito, M.; Tsukuda, K.; Whipple, E. B.; Watts, P. C.; Moppett, C. E.; Jefferson, M. T.; Huang, L. H.; Cullen, W. P.; Celmer, W. D. 20th Interscience Conference on Antimicrobial Agents and Chemotherapeutics; New Orleans, LA, 1980, pp 22-24.
9. (d) Nodusmycin: Whaley, H. A.; Chidester, C. G.; Mizak, S. A.; Wnuk, R. J. Tetrahedron Lett. 1980, 21, 3659.
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28. (b) Yoda, Y.; Nakaseko, K.; Takabe Tetrahedron Lett. 2004, 45, 4217.
29. Sorg, A.; Brückner, R. Synlett 2005, 289.
30. (a) For a review see: Duncton, M. A. J.; Pattenden, G. J. Chem. Soc., Perkin Trans, 1 1999, 1235 and references therein.
31. w = 0.1003 (for 1969 data and 173 refined parameters). CCDC 602228 contains the supplementary crystallographic data. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.