Synthetic approaches towards laulimalide: Synthesis of the C12-C29 fragment

Synlett

Volumn , Issue 11, 1998, Pages 1209-1210

  Shimizu, Atsushi ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001030047     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1934     Document Type: Article

References (13)

1. Corley, D. G.; Herb, R.; Moore, R. E.; Scheuer, P. J.; Paul, V. J. J. Org. Chem. 1988, 53, 3644.
2. Fijianolide B has the same relative structure as laulimalide: Quiñoà, E.; Kakou, Y.; Crews, P. J. Org. Chem. 1988, 53, 3642.
3. Jefford, C. W.; Bernardinelli, G.; Tanaka, J.; Higa, T. Tetrahedron Lett. 1996, 37, 159.
4. CAS online indicated that the following investigations had been published.
5. a) Upinder, S. Diss. Abstr. Int. B 1995, 55, 4858.
6. b) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427.
7. Julia, M.; Paris, J. M. Tetrahedron Lett. 1973, 14, 4833.
8. Sharpless, K. B.; Michaelson, R. J. Am. Chem. Soc. 1973, 95, 6136.
9. Shimizu, A.; Nishiyama, S. Tetrahedron Lett. 1997, 38, 6011.
10. Ravid, U.; Silverstein, R.; Smith, L. R. Tetrahedron 1978, 34, 1449.
11. Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1971, 10, 330.
12. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373.
13. 3): 8: δ 1.06 (9H, s), 2.35 (1H, dd, J=7.92, 13.8 Hz), 2.46 (1H, dd, J=5.28, 13.8 Hz), 3.79 (3H, s), 3.83 (1H, ddd, J=1.98, 5.28, 7.92 Hz), 4.12 (2H, s). 4.40 (1H, d, J=11.5 Hz), 4.48 (1H, d, J=11.5 Hz), 4.99 (1H, s), 5.27 (1H, s), 6.82 (2H, d, J=8.58 Hz), 7.16 (2H, d, J=8.58 Hz), 7.34-7.46 (6H, complex), 7.64-7.68 (4H, complex), 9.55 (1H, d, J=1.98 Hz). 9: δ 1.35 (6H, s), 1.84-2.17 (4H, complex), 3.15 (1H, ddd, J=4.62, 11.2, 13.9 Hz), 3.67 (1H, ddd, 1H, J=4.95, 11.6, 13.9 Hz), 3.67 (1H, ddd, J=3.30, 8.58, 11.9 Hz), 3.97-4.07 (2H, complex), 4.19 (2H, brs), 5.42 (1H, brs), 5.65 (1H, dd, J=6.92, 15.5 Hz), 5.89 (1H, dd, J=5.28, 15.5 Hz), 7.55-7.70 (3H, complex), 7.90-7.93 (2H, complex). 3: δ 1.42 (3H, s), 1.43 (3H, s), 1.70 (3H, s), 1.91 (1H, brd), 2.05 (1H, m), 2.34-2.51 (4H, complex), 3.77 (1H, m), 3.80 (3H, s), 3.86-3.95 (3H, complex), 4.03-4.12 (2H, complex), 4.18 (2H, brs), 4.27 (1H, d, J=11.7 Hz), 4.51 (1H, d, J=11.7 Hz), 4.95 (1H, s), 5.28 (1H, s), 5.41 (1H, brs), 5.47 (1H, dd, J=7.81, 15.4 Hz), 5.68-5.75 (2H, complex), 5.90 (1H, ddd, J=3.91, 5.37, 16.2 Hz), 6.86 (2H, d, J=8.3 Hz), 7.22 (2H, d, J=8.3 Hz).