Isomerization - Cyclization Approach to the Synthesis of 2-Hydroxy-5-alkylidene-cyclopent-2-enones

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4069-4072

  Forest, Jeremy ^a,b   Bee, Cisco ^a,b   Cordaro, Frank ^a,b   Tius, Marcus A ^a,b  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF HAWAII CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENE DERIVATIVE; ENAMINE; KETONE DERIVATIVE; MORPHOLINE DERIVATIVE; SILICA GEL;

ADDITION REACTION; ARTICLE; CYCLIZATION; ISOMERISM; SYNTHESIS;

CYCLIZATION; CYCLOPENTANES; ETHERS; ISOMERISM; MOLECULAR STRUCTURE; SILICON DIOXIDE;

EID: 0344944952     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035498z     Document Type: Article

References (15)

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5. For a review of the Nazarov reaction, see: Habermas, K. L.; Denmark, S.; Jones, T. K. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1994; Vol. 45, pp 1-158.
6. For an overview of our work in this area, see: Tius, M. A. Acc. Chem. Res. 2003, 36, 284-290 and references cited therein.
7. Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1968, 87, 916-924.
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9. Tius, M. A.; Gomez-Galeno, J.; Gu, X.-Q.; Zaidi, J. H. J. Am. Chem. Soc., 1991, 113, 5775-5783.
10. Bee, C.; Tius, M. A. Org. Lett. 2003, 5, 1681-1684.
11. 3), whereas in the (E)-isomers, the C6 methine proton appears near 6.6 ppm.
12. Hu, H.; Smith, D.; Cramer, R. E.; Tius, M. A. J. Am. Chem. Soc. 1999, 121, 9895-9896.
13. Configuration in 20 and 25 was established unambiguously on the basis of a positive NOE, in the case of 20 between the tert-butyl and the C4 methylene protons, and in the case of 25 between the C6 methine and the C4 methylene protons. The stereochemistry of 26 and 27 was also determined on the basis of the NOE between C4 and C6 methine protons.
14. There is precedent for such donor - acceptor interactions: Macharashvili, A. A.; Shklover, V. E.; Struchkov, Yu. T.; Baukov, Yu. I.; Kramarova, E. P.; Oleneva, G. I. J. Organomet. Chem. 1987, 327, 167-172.
15. Jang, W. B.; Hu, H.; Lieberman, M. M.; Morgan, J. A.; Stergiades, I. A.; Clark, D. S. Tius, M. A. J. Comb. Chem. 2001, 3, 346-353.