A new stereoselective route to (-)-octalactin A based on intramolecular SmI2 promoted Reformatsky reaction

Synlett

Volumn , Issue 7, 1998, Pages 735-736

  Inoue, Susumu ^a   Iwabuchi, Yoshiharu ^a   Irie, Hiroshi ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000342583     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1778     Document Type: Article

References (17)

1. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682.
2. (a) Buszek, K. R.; Sato, N.; Jeong, Y. J. Am. Chem. Soc. 1994, 116, 5510.
3. (b) McWilliams, J. C.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 8378.
4. (c) Bach, J.; Berenguer, R.; Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1995, 36, 3425.
5. (d) Buszek, K. R.; Jeong, Y. Tetrahedron Lett. 1995, 36, 7189.
6. (e) Andrus, M. B.; Argade, A. B. Tetrahedron Lett. 1996, 37, 5049.
7. (f) Kodama, M.; Matsushita, M.; Terada, Y.; Takeuchi, A.; Yoshio, S.; Fukuyama, Y. Chem. Lett. 1997, 117.
8. (g) Hulme, A. N.; Howells, G. E. Tetrahedron Lett. 1997, 38, 8245.
9. 2 promoted reactions, see: Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
10. Tabuchi, T.; Kawamura, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 3889.
11. 3) data are following. 12: 7.35-7.25 (m, 5H), 4.54 (q, 1H, J = 7.6 Hz), 4.47 (s, 2H), 3.56 (dd, 1H, J = 9.3, 4.8 Hz), 3.53 (dt, 1H, J = 4.3, 10.1 Hz), 3.39 (dd, 1H, J = 9.3, 4.3 Hz), 2.78 (t, 1H, J = 12.1 Hz), 2.73 (dd, 1H, J = 12.1, 4.3 Hz), 2.36 (br s, 1H), 2.08-1.98 (m, 1H), 1.72-1.64 (m, 2H), 1.52 (dq, 1H, J = 9.5, 6.9 Hz), 1.45 (dt, 1H, J = 15.8, 4.1 Hz), 1.10 (d, 3H, J = 6.9 Hz), 1.30-1.18 (m, 1H), 1.02 (d, 3H, J = 7.0 Hz); 172.6, 138.3, 128.4, 127.6, 78.4, 75.3, 73.2, 71.4, 40.8, 39.6, 38.3, 32.1, 27.7, 21.0, 13.7. 13: 7.36-7.27 (m, 5H), 4.46 (s, 2H), 4.47 (q, 1H, J = 7.8 Hz), 3.99 (br s, 1H), 3.60 (dd, 1H, J = 9.0, 4.6 Hz), 3.38 (dd, 1H, J = 9.0, 4.0 Hz), 2.84 (dd, 1H, J = 13.0, 1.8 Hz), 2.68 (dd, 1H, J = 13.0, 6.3 Hz), 2.11 (brs, 1H), 2.04-1.97 (m, 1H), 1.78-1.61 (m, 4H), 1.20-1.16 (dt, 1H, J = 14.4, 4.1 Hz), 1.11 (d, 3H, J = 7.1 Hz), 1.02 (d, 3H, J = 7.1 Hz); 172.8, 138.3, 128.4, 127.8, 78.5, 73.2, 71.4, 53.5, 39.1, 38.3, 38.1, 32.0, 23.8, 21.7, 13.9. 14: 4.37 (ddd, 1H, J = 10.8, 8.0, 4.0 Hz), 3.94 (dt, 1H, J = 6.5, 2.0 Hz), 3.76 (br d, 1H, J = 10.5 Hz), 3.59 (br d, 1H, J = 10.5 Hz), 2.72 (dd, 1H, J = 12.6, 2.3 Hz), 2.65 (dd, 1H, J = 12.6, 6.6 Hz), 2.04-1.85 (m, 2H), 1.75-1.62 (m, 3H), 1.12(dt, 1H, J= 15.3, 4.3 Hz), 1.03 (d, 3H, J = 7.1 Hz), 1.00 (d, 3H, J = 7.1 Hz), 0.91 (s, 9H), 0.17 (s, 3H), 0.05 (s, 3H); 171.7, 79.2, 73.0, 64.5, 40.3, 39.8, 38.7, 31.6, 25.8, 23.6. 21.0, 18.1, 13.6, -4.2, -5.2. 2 (R = TBS): 9.73 (d, 1H, J= 1.4 Hz), 4.65 (ddd, 1H, J = 11.9, 7.3, 3.2 Hz), 3.96 (d, 1H, J = 6.6 Hz), 2.78 (dd, 1H, J= 12.8, 1.8 Hz), 2.74 (dt, 1H, J = 1.6, 7.3 Hz), 2.69 (dd, 1H, J = 12.8, 6.6 Hz), 2.02-1.93 (m, 1H), 1.78-1.54 (m, 5H), 1.13 (d, 3H, J = 7.6 Hz), 1.04 (d, 3H, J = 7.1 Hz), 0.91 (s, 9H), 0.18 (s, 3H), 0.05 (s, 3H); 202.4, 170.8, 72.8, 50.6, 39.7, 38.6, 31.4, 25.8, 23.1, 21.5, 18.1, 10.5, -4.2, -5.1.
12. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Org. Chem. 1987, 109, 5765.
13. This operation was neccessary to remove the corresponding 1,2-diol.
14. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156.
15. Swern oxidation of 12 always produced 9-benzyloxy-2,2-dichloro-4,8-dimethyl-3-oxo-7-nonanolide as a major product due to chlorination of initially formed 9-benzyloxy-4,8-dimethyl-3-oxo-7-nonanolide.
16. Reduction of the corresponding β-keto lactone proceeded with complete diastereoselectivity. This stereochemical outcome could arise from the conformational rigidity of the eight-membered β-keto lactone ring system. Cf.: Petasis, N. A.; Patane, M. A. J. Chem. Soc., Chem. Commun. 1990, 836.
17. The specific rotation was measured by Clardy and McWilliams.