Synthesis of the fully functionalized tris-oxazole fragment pound in metabolites derived from marine organisms

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5445-5448

  Liu, Ping ^a   Celatka, Cassandra A ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; OXAZOLE DERIVATIVE;

ARTICLE; METABOLITE; METHODOLOGY; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0030792962     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01218-5     Document Type: Article

References (17)

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7. The full stereochemistry of kabiramide C and halichondramide has not been unambiguously assigned.
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9. Yoo, S.-K. Tetrahedron Lett. 1992, 33, 2159-2162.
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11. (a) Aguilar, E.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 2473-2476.
12. (b) Wiley, R. H.; England, D. C.; Behr, C. C. Org. Reac. 1951, 6, 367-409.
13. The α,β-unsaturation of the amide was found to play a pivotal role in the formation of oxazoles, as alkyl and α-alkoxy amides did not effectively participate in the oxazole synthesis.
14. VanRheenen, V.; Kelley, R. C.; Cha, D. J. Org. Chem. 1978, 43, 2480-2482.
15. 6Si: 543.1825. Found: 543.1782.
16. The control of the reaction time for this reduction step is critical. If the reaction time was less than 5 minutes, approximately 20% of starting material ester remained intact; while if the reaction was allowed to proceed for more than 10 minutes, approximately 20% of the ester was overreduced to the alcohol. A reaction time of 7-8 minutes gave the best results.
17. 5Si: 517.6365. Found: 517.1932.