Synthesis of th C1-C16 fragment of the marine toxin, laulimalide

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 6011-6014

  Shimizu, Atsushi ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LAULIMALIDE; MARINE TOXIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030785757     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01336-1     Document Type: Article

References (12)

1. a) Corley, D. G.; Herb, R.; Moore, R. E.; Scheuer, P. J.; Paul, V. J. J. Org. Chem. 1988, 53, 3644.
2. b) Fijianolide B has the same relative structure as laulimalide: Quiñoà, E.; Kakou, Y.; Crews, P. J. Org. Chem. 1988, 55, 3642.
3. Jefford, C. W.; Bemardinelli, G.; Tanaka, J.; Higa, T.; Tetrahedron Lett. 1996, 37, 159.
4. During preparation of this manuscript, a related investigation has been published: Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427.
5. Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.; Hwang, C. K. J. Am. Chem. Soc. 1993, 155, 3558.
6. Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem. Int. Ed. Engl. 1996, 35, 904.
7. Ravid, U.; Silverstein, R.; Smith, L. R. Tetrahedron 1978, 34, 1449.
8. Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Angew. Chem. Int. Ed. 1971, 10, 330.
9. 11 position was determined by N.O.E. experiments of the corresponding seven-membered lactone synthesized as depicted in Scheme 6. equation presented
10. Tabusa, F.; Yamada, T.; Suzuki, K.; Mukaiyama, T. Chem. Lett. 1984, 405.
11. 2 (M+): m/z 542.3819. Found: m/z 542.3814.
12. An instability of 16 under the reaction conditions caused an inseparable mixture of minor products, and the starting material could not be recovered. The corresponding E-isomer could not be obtained in this case.