Synthesis of slagenins A, B, and C

Organic Letters

Volumn 2, Issue 22, 2000, Pages 3443-3444

  Sosa, Ana Carolina Barrios ^a   Yakushijin, Kenichi ^a   Horne, David A ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIN; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURAN DERIVATIVE; IMIDAZOLE DERIVATIVE; SLAGENIN A; SLAGENIN B; SLAGENIN C;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SPONGE (PORIFERA); SYNTHESIS;

ANIMALS; CYTOTOXINS; FURANS; IMIDAZOLES; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PORIFERA;

EID: 0000741983     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000233v     Document Type: Article

References (12)

1. Tsuda, M.; Uemoto, H.; Kobayashi, J. Tetrahedron Lett. 1999, 40, 5709.
2. Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C.; Valencia, C. Tetrahedron 1993, 49, 2676.
3. Olofson, A.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 1998, 63, 1248.
4. Initially performed with thiocyanate, see: (a) Akabori, S. Ber. 1933, 66, 157.
5. (b) Lawson, A.; Morley, H. V. J. Chem. Soc. 1955, 1695.
6. 13C NMR and HRMS).
7. Acid-facilitated dimerization of 7 and/or 8 predominates under these conditions. Current efforts are underway to optimize this step.
8. MacManus, S. P.; Carroll, J. T. J. Org. Chem. 1970, 35, 3768.
9. Keifer, P. A.; Schwartz, R. E.; Koker, M. E. S.; Hughes, R. G., Jr.; Rittschof, D.; Rinehart, K. L. J. Org. Chem. 1991, 56, 2965.
10. Initial acid cleavage led to an intermediate ester which upon treatment with base facilited acyl transfer producing amide 4.
11. 13C chemical shift values in ref 1 are noted in a personal communication from Professor Kobayashi: C2 of slagenin A should be 120.7 ppm and the listed values for C8 of slagenins B and C should be interchanged.
12. Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 7 and earlier reports in this series.