Radical cyclization of β-alkoxymethacrylates: Expedient synthesis of (+)-methyl nonactate

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1127-1128

  Lee, Eun ^a   Choi, Seung Jib ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001082090     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9909536     Document Type: Article

References (23)

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2. (b) Lee, E.; Tae, J. S.; Chong, Y. H.; Park, Y. C.; Yun, M.; Kim, S. Tetrahedron Lett. 1994, 35, 129.
3. (c) Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293.
4. (d) Lee, E.; Jeong, J.-w.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
5. Lee, E.; Park, C. M.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017.
6. Lee, E.; Yoo, S.-K.; Cho, Y.-S.; Cheon, H.-S.; Chong, Y. H. Tetrahedron Lett. 1997, 38, 7757.
7. Lee, E.; Yoo, S.-K.; Choo, H.; Song, H. Y. Tetrahedron Lett. 1998. 39, 317.
8. More recently, the scope of radical cyclization reactions of β-alkoxyacrylates expanded considerably; see the following references: (a) Use of acyl radicals: Evans, P. A.; Roseman, J. D.; Garber, L. T. J. Org. Chem. 1996, 61, 4880 and references therein.
9. (b) Formation of oxepanes in the presence of a Lewis acid: Yuasa, Y.; Sato, W.; Shibuya, S. Synth. Commun. 1997, 27, 573.
10. Photosensitized electron-transfer cyclization of aldehydes: Pandey, G.; Hajra, S.; Ghorai, M. K.; Kumar, R. J. Org. Chem. 1997, 62, 5966.
11. 2-induced cyclization of aldehydes: Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811.
12. (e) O-Linked oxepane synthesis: Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337.
13. (a) Guindon, Y.; Lavallée, J.-F.; Boisvert, L.; Chabot, C.; Delorme, D.; Yoakim, C.; Hall, D.; Lemieux, R.; Simoneau, B. Tetrahedron Lett. 1991, 32, 27.
14. (b) Durkin, K.; Liotta, D.; Rancourt, J.; Lavallée, J.-F.; Boisvert, L.; Guindon, Y. J. Am. Chem. Soc. 1992, 114, 4912.
15. A large number of reports concern the synthesis of nonactic acid derivatives. Three of the more recent ones are as follows: (a) Lee, J. Y.; Kim, B. H. Tetrahedron 1996, 52, 571.
16. (b) Mandville, G.: Girad, C.; Bloch, R. Tetrahedron 1997, 53. 17079.
17. (c) Meiners, U.; Cramer, E.; Frölich, R.; Wibbeling, B.; Metz, P. Eur. J. Org. Chem. 1998, 2073.
18. (a) Mahler, U.; Devant, R. M.; Braun, M. Chem. Ber. 1988, 121, 2035.
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20. Reetz, M. T.; Kesseler, K.; Jung, A. Tetrahedron Lett. 1984, 25, 729.
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22. "Erythro" selectivity was reported for chelation-controlled reductions of α-substituted β-alkoxy-α-iodo carboxylates in the presence of Lewis acids: Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. This selectivity originates from reactions of chelated forms of the substrate α-iodo carboxylates. Obviously, the α-carbonyl radicals obtained from the cyclixation step engage in hydrogen abstraction oblivious to the Lewis acid in our case.
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