Preparation of E-secolupane acids and lactones

Collection of Czechoslovak Chemical Communications

Volumn 68, Issue 4, 2003, Pages 751-778

  Tišlerová, Iva ^a   Klinotová, Eva ^a   Klinot, Jiří ^a   Sejbal, Jan ^a,b   Rejzek, Martin ^a   Hilgard, Stanislav ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Lupane; NMR spectroscopy, 1H and 13C; Secolupane; Triterpenes; Triterpenoids

Indexed keywords

18 BETA,19 BETA EPOXY 21,22 DIOXOLUPANE 3 BETA,28 DIYLDIACETATE; 18 BETA,19 EPOXY 3 BETA,28 DIHYDROXY 21,22 SECOLUPANE 21,22 DIOIC ACID 21,28 LACTONE 22 METHYL ESTER; 3 BETA ACETOXY 18 BETA,19 EPOXY 28 HYDROXY 21,22 SECOLUPANE 21,22 DIOIC ACID 21,28 LACTONE 22 METHYL ESTER; 3 BETA ACETOXY 19 HYDROXY 21,22 SECOLUPANE 21,28:22 18 ALPHA DILACTONE; 3 BETA ACETOXY 19 HYDROXY 22 NOR 21,22 SECOLUP 17 ENE 21,28 LACTONE; 3 BETA ACETOXY 19 OXO 21,28 DINOR 19,21 SECOLUPAN 22 OIC ACID; 3 BETA ACETOXY 21,28 DINOR 19,21 SECOLUP 17 ENE 22,19 LACTONE; 3 BETA HYDROXY 19 OXO 21,28 DINOR 19,21 SECOLUPAN 22 OIC ACID; 3 BETA HYDROXY 21,28 DINOR 19,21 SECOLUP 17 ENE 22,19 LACTONE; 3 BETA,19 DIHYDROXY 21,22 SECOLUPANE 21,28:22,18 ALPHA DILACTONE; 3 BETA,19 DIHYDROXY 22 NOR 21,22 SECOLUP 17 ENE 21,28 LACTONE; 3 BETA,28 DIACETOXY 18 BETA,19 EPOXY 21,22 SECOLUPANE 21,22 DIOIC ACID; 3 BETA,28 DIACETOXY 18 BETA,19 EPOXY 21,22 SECOLUPANE 21,22 DIOIC ACID ANHYDRIDE; 3 BETA,28 DIACETOXY 21,22 SECOLUP 18 ENE 21,22 DIOIC ACID; 3 BETA,28 DIHYDROXY 18 BETA,19 EPOXY 21,22 SECOLUPANE 21,22 DIOIC ACID 21,28 LACTONE; ACID; ALKALI; CARBON; CARBONYL DERIVATIVE; DICARBOXYLIC ACID; DIMETHYL 3 BETA ACETOXY 18 BETA,19 EPOXY 28 HYDROXY 21,22 SECOLUPANE 21,22 DIOATE; DIMETHYL 3 BETA,28 DIACETOXY 18 BETA,19 EPOXY 21,22 SECOLUPANE 21,22 DIOATE; EPOXIDE; LACTONE DERIVATIVE; METHYL 3 BETA ACETOXY 19 OXO 21,28 DINOR 19,21 SECOLUPAN 22 OATE; METHYL 3 BETA HYDROXY 19 OXO 21,28 DINOR 19,21 SECOLUPAN 22 OATE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; DECARBOXYLATION; HYDROLYSIS; INFRARED RADIATION; ISOLATION PROCEDURE; MASS SPECTROMETRY; MEASUREMENT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 0038292958     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20030751     Document Type: Article

References (16)

1. Sejbal J., Homolová M., Tišlerová I., Křeček V.: Collect. Czech. Chem. Commun. 2000, 65, 1339.
2. Soler F., Poujade C., Evers M., Carry J.-C., Hénin Y., Bousseau A., Huet T., Pauwels R., De Clercq E., Mayaux J.-F., Le Pecq J.-B., Dereu N.: J. Med. Chem. 1996, 39, 1069.
3. Fujioka T., Kashiwada Y., Kilkuskie R. E., Cosentino L. M., Ballas L. M., Jiang J. B., Janzen W. P., Chen I. S., Lee K. H.: J. Nat. Prod. 1994, 57, 243.
4. a) Sun I. C., Wang H. K., Kashiwada Y., Shen J. K., Cosentino L. M., Chen C. H., Yang L. M., Lee K. H.: J. Med. Chem. 1998, 41, 4648;
5. b) Kashiwada Y., Chiyo J., Ikeshiro Y., Nagao T., Okabe H., Cosentino L. M., Fowke K., Lee K. H.: Bioorg. Med. Chem. Lett. 2001, 11, 183.
6. Kim D. S. L., Pezzuto J. M., Pisha E.: Bioorg. Med. Chem. Lett. 1998, 8, 1707.
7. Lee S. S., Chen W. C., Huang C. F., Su Y.: J. Nat. Prod. 1998, 61, 1343.
8. Ryu S. Y., Choi S. U., Lee S. H., Lee C. O., No Z., Ahn J. W.: Arch. Pharm. Res. 1994, 17, 375.
9. Ngassapa O. D., Soejarto D. D., Che C. T., Pezzuto J. M., Farnsworth N. R.: J. Nat. Prod. 1991, 54, 1353.
10. a) Sturm S., Gil R. R., Chai H. B., Ngassapa O. D., Santisuk T., Reutrakul V., Howe A., Moss M., Besterman J. M., Yang S. L., Farthing J. E., Tait R. M., Lewis J. A., O'Neil M. J., Farnsworth N. R., Cordell G. A., Pezzuto J. M., Kinghorn A. D.: J. Nat. Prod. 1996, 59, 658;
11. b) Mi Q. W., Lantvit D., Reyes-Lim E., Chai H. Y., Zhao W. M., Lee I. S., Peraza-Sanchez S., Ngassapa O., Kardono L. B. S., Riswan S., Hollingshead M. G., Mayo J. G., Farnsworth N. R., Cordell G. A., Kinghorn A. D., Pezzuto J. M.: J. Nat. Prod. 2002, 65, 842.
12. Rice G. K., Yokoi T., Hayashi T., Suzuki H., Lee K. H., McPhail A.: J. Chem. Soc., Chem. Commun. 1986, 1377.
13. Sejbal J., Klinot J., Buděšínský M., Protiva J.: Collect. Czech. Chem. Commun. 1991, 56, 2936.
14. Klinotová E., Rejzek M., Zůnová H., Sejbal J., Klinot J., Urban J.: Collect. Czech. Chem. Commun. 1993, 58, 2505.
15. Klinotová E., Čermáková J., Rejzek M., Křeček V., Sejbal J., Olšovský P., Klinot J.: Collect. Czech. Chem. Commun. 1999, 64, 329.
16. Hajdúch M.: Unpublished results.