Enantioselective synthesis of ancepsenolide and its analogs

Bioscience, Biotechnology and Biochemistry

Volumn 65, Issue 8, 2001, Pages 1903-1906

  Takai, Katsuki ^a   Iriye, Ryozo ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

Aldol reaction; Ancepsenolide; Butenolide; Optical resolution

Indexed keywords

STAPHYLOCOCCUS PHAGE 3A;

BUTENOLIDE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURAN DERIVATIVE; GAMMA BUTYROLACTONE;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; FURANS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 0035431328     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.65.1903     Document Type: Article

References (17)

1. Ciereszko, L. S., Sifford, D. H., and Weinheimer, A. J., Chemistry of coelenterates I. Occurrence of terpenoid compounds in gorgonians. Ann. N.Y. Acad. Sci., 90, 917-919 (1960).
2. Schmitz, F. J., Kraus, K. W., Ciereszko, L. S., Sifford, D. H., and Weinheimer, A. J., Ancepsenolide: A novel bisbutenolide of marine origin. Chemistry of coelenterates V. Tetrahedron Letters, 1, 97-104 (1966).
3. Schmitz, F. J., Lorance, E. D., and Ciereszko, L. S., Chemistry of Coelenterates XII. J. Org. Chem., 34, 1989-1990 (1969).
4. Guo, Y., Gavagunin, M., Mollo, E., Trivellone, E., and Cimino, G., Three new butenolide lipids from the Caribbean gorgonian Pterogorgia anceps. J. Nat. Prod., 62, 1194-1196 (1999).
5. Rodriguez, A. D. and Ramírez, C., Further butenolides from the Caribbean octocoral, Pterogorgia citrina. J. Nat. Prod., 57, 339-347 (1994).
6. Schmitz, F. J. and Lorance, E. D., Chemistry of coelenterates XXI. Lactones from the gorgonian Pterogorgia guadalupensis. J. Org. Chem., 36, 719-721 (1971).
7. Rupprecht, J. K., Hui, Y., and McLaughlin, J. L., Annonaceous acetogenins: a review. J. Nat. Prod., 53, 237-278 (1990).
8. Fang, X., Rieser, M. J., Gu, Z., Zhao, G., and McLaughlin, J. L., Annaceous acetogenins: An update review. Phytochem. Anal., 4, 27-48 (1993).
9. Cavé, A., Figadère, B., Laurens, A., and Cortes, D., Acetogenins from Annonaceae. In "Progress in the Chemistry of Natural Products," eds. Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., and Tamm, Ch., Springer, Wien, 70, pp. 81-288 (1997).
10. Alali, F. Q., Liu, X., and McLaughlin, J. L., Annoceous acetogenins: Recent progress. J. Nat. Prod., 62, 504-540 (1999).
11. Hoppen, S., Emide, U., Friedrich, T., Grubert, L., and Koert, U., Natural-product hybrids: Design, synthesis, and biological evaluation of quinone-annonaceous acetogenins. Angew. Chem. Int. Ed., 39, 2099-2102 (2000).
12. Podraza, K. F. and Sneden, A. T., A short synthesis of ancepsenolide. J. Nat. Prod., 48, 792-795 (1985).
13. Trost, B. M., Müller, T. J. J., and Martinez, J., Ruthenium catalyzed synthesis of butenolides and pentenolide via contra-electronic α-alkylation of hydroxyalkynoates. J. Am. Chem. Soc., 117, 1888-1899 (1995).
14. Iriye, R., Nakamura, A., and Takeshita, M., Synthesis of 2-(2-hydroxyalkylidene)cyclopentanones and their bio-antimutagenic activity. Biosci. Biotechnol. Biochem., 59, 401-407 (1995).
15. -. Bioorg. Med. Chem. Lett., 7, 199-202 (1997).
16. Noguchi, M., Takai, K., Takei, Y., and Iriye, R., Synthesis of (R)-and (S)-13-hydroxy-10-oxo-trans-11-octadecenoic acid and their antimutagenic activity. Biocontrol Sci., 5, 91-95 (2000).
17. van Delft, F. L., Timmers, C. M., van der Marel, G. A., and van Boom, J. H., Preparation of 2-oxazolidinones by intramolecular nucleophilic substitution. Synthesis, 450-454 (1997).