Synthesis of the C8-C15 segment of (+)-discodermolide

Chemistry Letters

Volumn , Issue 12, 1997, Pages 1193-1194

  Miyazawa, Masahiro ^a   Oonuma, Satoshi ^a   Maruyama, Kimiyuki ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002677983     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.1193     Document Type: Article

References (11)

1. M. Miyazawa, S. Oonuma, K. Maruyama, and M. Miyashita, preceding paper.
2. N. Nakajima, K. Horita, R Abe, and O. Yonemitsu, Tetrahedron Lett., 29, 4139 (1988).
3. T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 102, 5974 (1980).
4. M. R. Johnson, T. Nakata, and Y. Kishi, Tetrahedron Lett., 1979, 4343.
5. 12 positions, the methylation of 16 with trimethylaluminum (10 equiv.) in dichloroethane in the presence of water (6 equiv.) was examined and the desired product 17 was obtained as a single product. Equation presented.
6. Oxidation of 11 with Swern oxidation resulted in poor yield of the product.
7. D. B. Dess and J. C. Martin, J. Org. Chem., 48, 4155 (1983).
8. A. B. Smith, III, S. M. Condon, J. A. McCauley, J. L. Leazer, Jr., J. W. Leahy, and R. E. Maleczka, Jr., J. Am. Chem. Soc., 117, 5407 (1995).
9. K. Ando, Tetrahedron Lett., 36, 4105 (1995), K. Ando, J. Org. Chem., 62, 1934 (1997).
10. K. Ando, Tetrahedron Lett., 36, 4105 (1995), K. Ando, J. Org. Chem., 62, 1934 (1997).
11. 3) δ 0.06 (s, 3H), 0.07 (s, 3H), 0.57 (q, J = 7.9 Hz, 6H), 0.92 (s, 9H), 0.99 (t, J = 7.9 Hz, 9H), 1.00 (d, J = 6.9 Hz, 3H), 1.17 (d, J = 7.3 Hz, 3H), 1.81 (d, J = 1.2 Hz, 3H), 2.64 (dq, J = 2.6, 7.3 Hz, 1H), 2.84 (ddq, J = 10.6, 6.9, 6.9 Hz, 1H), 3.31 (dd, J = 2.6, 7.2 Hz, 1H), 3.97 (d, J = 10.9 Hz, 1H), 4.35 (d, J = 10.9 Hz, 1H), 5.21 (dq, J = 10.6, 1.2 Hz, 1H).