Synthesis of optically active 14α- and 14β-cheilanthanic esters

Synthesis

Volumn , Issue 14, 2006, Pages 2385-2391

  Ungur, Nicon ^a,b   Kulciţki, Veaceslav ^a,b   Gavagnin, Margherita ^a   Castelluccio, Francesco ^a   Cimino, Guido ^a  

^a CNR   (Italy)

^b Institutul de Chimie al Academiei de Ştiinţe a RM ^*  (Moldova)

Author keywords

Cyclizations; Esters; Rearrangements; Synthesis; Terpenoids

Indexed keywords

ALCOHOLS; CARBON; STEREOCHEMISTRY; SUBSTRATES; SYNTHESIS (CHEMICAL);

CYCLIZATIONS; REARRANGEMENTS; SYNTHONS; TERPENOIDS;

ESTERS;

14ALPHA CHEILANTHANIC ESTER; 14BETA CHEILANTHANIC ESTER; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 33746657644     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942386     Document Type: Article

References (21)

1. Hanson, J. R. Nat. Prod. Rep. 1996, 13, 529; and earlier reviews in this series.
2. Blunt, J. W.; Copp, B. R.; Munro, M. G. H.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2006, 23, 26; and earlier articles in this series.
3. Crews, P.; Jimenez, C. J.; Neil-Johnson, M. O. Tetrahedron 1991, 47, 3585.
4. Lai, A. R.; Gambie, R. C.; Rickard, C. E. F.; Bergquist, P. R. Tetrahedron Lett. 1994, 35, 2603.
5. Gomez-Paloma, L.; Randazzo, A.; Minale, L.; Debitus, C.; Roussakis, C. Tetrahedron 1997, 53, 10451.
6. Randazzo, A.; Debitus, C.; Minale, L.; Garca Pastor, P.; Alcaraz, M. J.; Payà, M.; Gomez-Paloma, L. J. Nat. Prod. 1998, 61, 571.
7. De Marino, S.; Iorizzi, M.; Zollo, F.; Debitus, C.; Menou, J.-L.; Ospina, L. F.; Alcaraz, M. J.; Payà, M. J. Nat. Prod. 2000, 63, 322.
8. Buchanan, M. S.; Edser, A.; King, G.; Whitmore, J.; Quinn, R. J. J. Nat. Prod. 2001, 64, 300.
9. De Carvalho, M. S.; Jacobs, R. S. Biochem. Pharmacol. 1991, 42, 1621.
10. Potts, B. C. M.; Faulkner, D. J.; De Carvalho, M. S.; Jacobs, R. S. J. Am. Chem. Soc. 1992, 114, 5093.
11. Ungur, N.; Kulciţki, V. Phytochem. Rev. 2004, 3, 401.
12. Sierra, M. G.; Gravero, R. M.; De los Angeles Laborde, M.; Ruveda, E. A. J. Chem. Soc., Perkin Trans. 1 1985, 1227.
13. (a) Ungur, N.; Nguen, V. H.; Vlad, P. F. Khim. Prir. Soedin. 1990, 353.
14. (b) Ungur, N.; Nguen, V. H.; Vlad, P. F. Chem. Nat. Compd. (Engl. Transl.) 1991, 26, 292.
15. Ungur, N.; Kulcitki, V.; Gavagnin, M.; Castelluccio, F.; Vlad, P. F.; Cimino, G. Tetrahedron 2002, 58, 10159.
16. Vlad, P. F.; Ungur, N. D.; Nguen, V. T. Russ. Chem. Bull. 1995, 44, 2404.
17. Herz, W.; Prasad, J. S. J. Org. Chem. 1982, 47, 4171.
18. Yee, N. K. N.; Coates, R. M. J. Org. Chem. 1992, 57, 4598.
19. Smit, W. A.; Semenovsky, A. V.; Kucherov, V. F. Izv. Akad. Nauk, Ser. Khim. 1959, 1848.
20. Vlad, P. F.; Ungur, N. D.; Barba, A. N.; Tatarova, L. E.; Gatilov, Y. V.; Korchagina, D. V.; Bagrianskaya, I. Y.; Gatilova, V. P.; Shmidt, E. N.; Barkhash, V. A. Zh. Org. Khim. 1986, 22, 2519;
21. J. Org. Chem. U.S.S.R. (Engl. Transl.) 1987, 23, 2261.