Total synthesis of (±)-dihydroprotolichesterinic acid and formal synthesis of (±)-Roccellaric acid by radical cyclisation of an epoxide. Using a transition-metal radical source

Tetrahedron

Volumn 55, Issue 37, 1999, Pages 11395-11398

  Mandal, Pijus Kumar ^a   Roy, Subhas Chandra ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Dihydroprotolichesterinic acid; Epoxide; Radical cyclisation; Roccellaric acid; Transition metal

Indexed keywords

DIHYDROPROTOLICHESTERINIC ACID; EPOXIDE; LACTONE DERIVATIVE; METAL; RADICAL; ROCCELLARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033543463     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00635-3     Document Type: Article

References (24)

1. (a) Grieco, P.A. Synthesis 1975, 67-82.
2. (b) Hoffman, H.M.R.; Rabe, J. Angew.Chem.Int.Ed.Engl. 1985, 24, 94-110.
3. (c) Petragnani, N.; Ferraz, H.M.C.; Silva, G.V.J. Synthesis 1986, 157-183.
4. (d) Collins, I. Contemporary Organic Synthesis, 1997, 4, 281-307.
5. (e) Dictionary of Organic Compounds: Chapman and Hall: New York, 1982.
6. (f) Comprehensive Medicinal Chemistry, Hansch, C., Ed.; Pergamon Press: Oxford, U.K. 1990.
7. (a) Ariza, J.; Font, J; Ortuno, R.M.; Tetrahedron 1990, 46, 1931-1942.
8. (b) Koch, S.S.C.; Chamberlin, A.R. J.Org.Chem. 1993, 58, 2725-2737.
9. (c) Menges, M.; Bruckner, R. Synlett 1993, 901-905.
10. (d) Nagao, Y.; Dai, W.M.; Ochiai, M.; Shiro, M. J.Org.Chem. 1989, 54, 5211-5217
11. a) Huneck, S.; Follmann, G.Z. Naturforsch.B 1967, 22, 666.
12. (b) Asano, M.; Azumi, T. Ber.Dt.Chem.Ges. 1935, 68, 995.
13. (c) Asahina, Y.; Yanagita, M. Ber.Dt.Chem.Ges. 1936, 69, 120.
14. Hesse, O.J. Prakt.Chem. 1898, 57, 232.
15. Cavallito, C.J.; Freuhauf, D.McK.; Bailey, J.H. J.Am.Chem.Soc 1948, 70, 3724-3726.
16. (a) Mulzer, J.; Salimi, N.; Hartl, H. Tetrahedron:Asymmetry 1993, 4, 457-471.
17. (b) Banks, M.R.; Dawson, I.M.; Gosney, I.; Hodgson, P.K.G.; Thornburn, P. Tetrahedron Lett. 1995, 36, 3567-3570.
18. (c) Takahata, H.; Uchida, Y.; Momose, T. J.Org.Chem. 1995, 60, 5628-5633.
19. (d) Sibi, M.P.; Deshpande, P.K.; LaLoggia, A.J. Synlett 1996, 343-345.
20. (e) Martin, T.; Rodriguez, C.M.; Martin, V.S. J.Org.Chem. 1996, 61, 6450-6453.
21. (f) Sibi, M.P.; Ji, J. Angew.Chem.Int.Ed.Engl., 1997, 36, 274-276.
22. (g) Chen, M.J.; Liu, R.S. Tetrahedron Lett. 1998, 39, 9465-9468.
23. Mandal, P.K.; Maiti, G.; Roy, S.C. J.Org.Chem., 1998, 63, 2829-2834.
24. Rajanbabu, T.V.; Nugent, W.A. J.Am.Chem.Soc. 1994, 116, 986-997 and references cited therein.