Photodegradation of some 14,15-bisnorlabdene-13-ones, derived from larixol. Synthesis of drimanic dienes with functional groups at C-6

Tetrahedron

Volumn 62, Issue 36, 2006, Pages 8489-8497

  Vlad, Pavel F ^a   Ciocarlan, Alexandru G ^a   Coltsa, Mihai N ^a   Deleanu, Calin ^b,c   Costan, Oana ^b,c   Simonov, Yurii A ^d   Kravtsov, Victor Ch ^d   Lipkowski, Janusz ^e   Lis, Tadeusz ^f   de Groot, Aede ^g  

^a INSTITUTE OF CHEMISTRY   (Moldova)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

^c National NMR Laboratory   (Romania)

^d INSTITUTE OF APPLIED PHYSICS   (Moldova)

^e INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

^f UNIVERSITY OF WROC AW   (Poland)

^g WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

14,15 Bisnorlabdene 13 ones; Chiral drimane synthons; Larixol; Norrish type II reactions; Photolysis

Indexed keywords

ALKADIENE; CARBON; SESQUITERPENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEGRADATION; PHOTODEGRADATION; PHOTOLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 33746757738     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.081     Document Type: Article

References (23)

1. Jansen B.J.M., and de Groot A. Nat. Prod. Rep. 8 (1991) 309-318
2. Jansen B.J.M., and de Groot A. Nat. Prod. Rep. 21 (2004) 449-477
3. Vlad P.F., Koltsa M.N., and Mironov G.N. Russ. Chem. Bull. 46 (1997) 855-873
4. Lagnel B.M.F., Morin C., and de Groot A. Synthesis (2000) 1907-1916
5. Bolster M.G., Jansen B.J.M., and de Groot A. Tetrahedron 57 (2001) 5663-5679
6. Bolster M.G., Lagnel B.M.F., Jansen B.J.M., Morin C., and de Groot A. Tetrahedron 57 (2001) 8369-8379
7. Bolster M.G., Jansen B.J.M., and de Groot A. Tetrahedron 58 (2002) 5275-5285
8. Ohloff G., Vial C., Wolf H.R., and Jeger O. Helv. Chim. Acta 59 (1976) 75-81
9. Berger J., Ioshioka M., Zink M.P., Wolf H.R., and Jeger O. Helv. Chim. Acta 63 (1980) 154-190
10. Nakano T., and Mailo M.A. Synth. Commun. 11 (1981) 463-473
11. Leite M.A.F., Sarragiotto M.H., Imamura P.M., and Marsaioli A.J. J. Org. Chem. 51 (1986) 5409-5410
12. Lithgow A.M., Marcos I.S., Basabe P., Sexmero J., Diez D., Gomez A., Estrella A., and Urones J.G. Nat. Prod. Lett. 6 (1995) 291-294
13. Vlad P.F., Aryku A.N., and Chokyrlan A.G. Russ. Chem. Bull. Int. Ed. 53 (2004) 443-446
14. Wahlberg I., Almqvist S.O., Nishida T., and Enzell C.R. Acta. Chem. Scand. B29 (1975) 1047-1058
15. Crystallographic data for the structures 20, 22, 23, 27 and 28 have been deposited at the Cambridge Crystallographic Data Centre as Supplementary Publication No. CCDC 279218, 279219, 279220, 279221 and 279222, respectively. Copies of the data can be obtained free of charge from CCDC (12 Union Road, Cambridge CB2 1EZ, UK; Tel.: +44 1223 336 408; fax: +44 1223 336 003; e-mail: deposit@ccdc.cam.ac.uk; www:http://ccdc.cam.ac.uk).
16. Sandermann W., and Bruns K. Chem. Ber. 99 (1966) 2835-2841
17. Romanchenko T.V., Schmidt E.N., and Pentegova V.A. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk 5 (1986) 120-123
18. Garlaschelli L., and Vidari G. Tetrahedron 45 (1989) 7371-7378
19. Mousseron-Canet M., and Chabaud J.P. Bull. Soc. Chim. Fr. (1969) 239-245
20. Iriarte J., Schaffner K., and Jeger O. Helv. Chim. Acta 46 (1963) 1579-1609
21. Altenburger E., Wehrli H., and Schaffner K. Helv. Chim. Acta 48 (1965) 704-710
22. Finucane B.M., and Thomson J.B. J. Chem. Soc. (1971) 1569-1570
23. Sheldrick G.M. SHELX-97, Program for the Solution and Refinement of Crystal Structures (1997), University of Gottingen, Germany