Chelation control in the [3+3] annulation reaction of alkoxy-substituted 1,1-diacylcyclopropanes with 1,3-bis(trimethylsilyloxy)-1,3-butadienes. Diversity-oriented synthesis of isochromanes

Journal of Organic Chemistry

Volumn 75, Issue 3, 2010, Pages 809-814

  Karapetyan, Vahuni ^a   Mkrtchyan, Satenik ^a   Hefner, Jennifer ^a   Fischer, Christine ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANNULATION REACTIONS; CHEMICAL EQUATIONS; DEPROTECTION; DIVERSITY-ORIENTED SYNTHESIS; FUNCTIONALIZED; METHOXY; OPENING REACTIONS;

CHELATION; CHLORINE COMPOUNDS; SYNTHESIS (CHEMICAL);

BUTADIENE;

1,3 BUS(TRIMETHYLSILYLOXY) 1,3 BUTADIENE DERIVATIVE; 1,3 BUTADIENE; ALKOXY 1,1 DIACYLCYCLOPROPANE DERIVATIVE; CHROMAN DERIVATIVE; ISOCHROMAN DERIVATIVE; PROPANE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

BUTADIENES; CATALYSIS; CHELATING AGENTS; CHROMANS; CYCLIZATION; CYCLOPROPANES; MOLECULAR STRUCTURE; STEREOISOMERISM; TRIMETHYLSILYL COMPOUNDS;

EID: 75749118916     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902334q     Document Type: Article

References (27)

1. Hepworth, J. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., eds.; Elsevier Science: Oxford, 1984; Vol. 3, p 737.
2. (a) Bavachromanol: Sohly, H. N.; Joshi, A. S.; Nimrod, A. C.; Walker, L. A.; Clark, A. M. Planta Med. 2001, 67, 87.
3. (b) Calyxin L: Tezuka, Y.; Gewali, M. B.; Ali, M. S.; Banskota, A. H.; Kadota, S. J. Nat. Prod. 2001, 64, 208.
4. Römpp-Lexikon Naturstoffe; Fugmann, B., Ed.;Georg Thieme Verlag: Stuttgart, 1997.
5. (a) Vismiaguianone E: Seo, E.-K.; Wani, M. C.; Wall, M. E.; Navarro, H.; Mukherjee, R.; Farnsworth, N. R.; Kinghorn, A. D. Phytochemistry 2000, 55, 35.
6. (b) Grandinal: Singh, I. P.; Hayakawa, R.; Etoh, H.; Takasaki, M.; Konoshima, T. Biosci. Biotechnol. Biochem. 1997, 61, 921.
7. (c) Calomelanol A: Asai, F.; Iinuma, M.; Tanaka, T.; Mizuno, M. Phytochemistry 1991, 30, 3091.
8. (d) Iryantherin E: Conserva, L. M.; Yoshida, M.; Gottlieb, O. R.; Martinez V., J. C.; Gottlieb, H. E. Phytochemistry 1990, 29, 3911.
9. Kock, I.; Draeger, S.; Schulz, B.; Elsässer, B.; Kurtan, T.; Kenez, A.; Antus, S.; Pescitelli, G.; Salvadori, P.; Speakman, J.-B.; Rheinheimer, J.; Krohn, K. Eur. J. Org. Chem. 2009, 1427.
10. Wang, Q.; Finn, M. G. Org. Lett. 2000, 2, 4063.
11. Jones, R. M.; Selenski, C.; Pettus, T. R. R. J. Org. Chem. 2002, 67, 6915.
12. Nguyen, V. T. H.; Appel, B.; Langer, P. Tetrahedron 2006, 62, 7674.
13. (a) Langer, P.; Bose, G. Angew. Chem., Int. Ed. 2003, 42, 4033.
14. (b) Bose, G.; Nguyen, V. T. H.; Ullah, E.; Lahiri, S.; Görls, H.; Langer, P. J. Org. Chem. 2004, 69, 9128.
15. For a review of [3+3] cyclizations, see: Feist, H.; Langer, P. Synthesis 2007, 327.
16. For a review of 1,3-bis(silyl enol ethers), see: Langer, P. Synthesis 2002, 441.
17. For reviews of chelation control in Lewis acid-mediated reactions, see: (a) Yamamoto, H. Lewis Acid Chemistry: A Practical Approach; Oxford University Press: Oxford, 1999.
18. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095.
19. (c) Santelli, M.; Pons, J. M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, 1996.
20. (d) Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 283-324.
21. Chelation control has been reported for the [4 + 3] annulation reaction of benzyloxy-substituted 1,4-dicarbonyl compounds with bis(silyl enol ethers): Molander, G. A.; Eastwood, P. R. J. Org. Chem. 1996, 61, 1910.
22. Hefner, J.; Langer, P. Tetrahedron Lett. 2008, 49, 4470.
23. Bruce, W. F.; Coover, H. W. J. Am. Chem. Soc. 1944, 66, 2092.
24. Wenner, W.; Plati, J. T. J. Org. Chem. 1946, 11, 751.
25. Gault, H.; Viout, A. Bull. Soc. Chim. Fr. 1951, 713.
26. (a) Chan, T.-H.; Brownbridge, P. J. Am. Chem. Soc. 1980, 102, 3534.
27. (b) Brownbridge, P.; Chan, T.-H.; Brook, M. A.; Kang, G. J. Can. J. Chem. 1983, 61, 688.