Synthesis of (±)-Homononactic Acid by Using cis-Selective Iodoetherification

Synlett

Volumn 1996, Issue 8, 1996, Pages 777-778

  Abe, Masaki ^a   Kiyota, Hiromasa ^a   Adachi, Michiaki ^a   Oritani, Takayuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0942275241     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5536     Document Type: Article

References (17)

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3. Schmidt, U.; Werner, J. J. Chem. Soc., Chem. Commun. 1986, 996.
4. Schmidt, U.; Werner, J. Synthesis 1986, 986.
5. Lygo, B. Tetrahedron 1988, 44, 6889.
6. Walkup, R. D.; Park, G. J. Am. Chem. Soc. 1990, 112, 1597.
7. Metz, P.; Meiners, U.; Cramer, E.; Fröhlich, R.; Wibbeling, B. Chem. Commun. 1996, 431.
8. Lee, J. Y.; Kim, B. H. Tetrahedron 1996, 52, 571 and references cited therein.
9. Bratt, K.; Garavelas, A.; Perlmutter, P.; Westman, G. J. Org. Chem. 1996, 61, 2109.
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11. Fräter, G. Helv. Chim. Acta 1979, 62, 2825; 2829.
12. The undesired syn-isomer was separated in final two steps.
13. Alexakis, A.; Gardette, M.; Colin, S. Tetrahedron Lett. 1988, 29, 2951.
14. Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963.
15. Marek, I.; Lefrançois, J-M.; Normant, J-F. Tetrahedron Lett. 1992, 33, 1747.
16. 3) δ 0.97 [d, 2.64H, J = 7.1 Hz, 7-Me of (7S*)-8], 1.01 [d, 0.36H, J = 7.1 Hz, 7-Me of (7R*)-8], 1.66-1.72 (m, 2H, 4-and 5-H), 1.73-2.00 (m, 2H, 5- and 7-H), 2.03-2.17 (m, 1H, 4-H), 2.52 (dd, 1H, J = 16.7, 5.2 Hz, 2-H), 2.58 (dd, 1H, J = 16.7, 5.5 Hz, 2-H), 3.42 (dd, J = 9.1, 6.5 Hz, 8-H), 3.55 (dd, 1H, J = 9.1, 4.7 Hz, 8-H), 3.82 (dt, 1H, J = 7.8, 6.3 Hz, 6-H), 4.12 (ddt, 1H, J = 7.2, 5.5, 5.2 Hz, 3-H), 4.51 (s, 2H, benzyl H), 7.23-7.38 (m, 5H, arom. H).
17. +, 212.1412; Found: 212.1401.