Regioselective synthesis of diterpenoid 1,2-diacyl-sn-glycerides

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4145-4148

  Fontana, Angelo ^a   Ungur, Nicon ^a,b   Gavagnin, Margherita ^a   Salierno, Ciro ^a   Cimino, Guido ^a  

^a CNR   (Italy)

^b INSTITUTE OF CHEMISTRY   (Moldova)

Author keywords

[No Author keywords available]

Indexed keywords

DIACYLGLYCEROL DERIVATIVE; DITERPENOID;

ACYLATION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030998883     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00806-X     Document Type: Article

References (17)

1. Associated to the National Institute for the Chemistry of Biological Systems (CNR).
2. Vance, D.E. Phospholipid metabolism and cell signalling in eucaryotes, in Biochemistry of Lipids, Lipoproteins and Membranes; Neuberger, A.; Van Deenen, L.L.M. Eds; Elsevier: Amsterdam, 1991; pp. 229-230.
3. Cimino, G.; Gavagnin, M.; Sodano, G.; Puliti, R.; Mattia, C.A.; Mazzarella, L. Tetrahedron 1988, 44, 2301-2310.
4. Davies-Coleman, M.T.; Faulkner, D.J. Tetrahedron, 1991, 47, 9743-9750.
5. Zubía, E.; Gavagnin, M.; Crispino, A.; Martinez, E.; Ortea, J.; Cimino, G. Experientia 1993, 49, 268-271.
6. Krug, P.J.; Boyd, K.G.; Faulkner, D.J. Tetrahedron, 1995, 51, 11063-11074.
7. Gavagnin, M.; Ungur, N.; Castelluccio, F.; Cimino, G. Tetrahedron 1997, 53, 1491-1504.
8. Gustafson, K.; Andersen, R.J. Tetrahedron, 1985, 41, 1101-1108.
9. De Petrocellis, L.; Orlando, P.; Gavagnin, M.; Ventriglia, M. C.; Cimino, G.; Di Marzo, V. Experientia 1996, 874-877.
10. Ungur, N.; Gavagnin, M.; Cimino, G. Tetrahedron Lett. 1996, 37, 3549-3552.
11. a. Copalic acid was obtained by the saponification of the corresponding methyl ester isolated from commercial "Copaiva Balsam" purchased from Lukas, W. Germany, as previously described in ref 8. b. Isocopalic acid was synthesized by superacidic cyclization of the copalic acid, according to the procedure previously reported in ref. 11 for the ent-isocopalic acid. c. (E,E,E)-Geranylgeranoic acid was obtained from (E,E)-farnesylacetone, as already reported by Vlad et al. in ref. 18.
12. Greene, T.W.; Wuts, P.G. Protective Groups in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1991; pp. 68-86.
13. Lipshutz, B.H.; Pollart, D.; Monforte, J.; Kotsuki, H. Tetrahedron Lett. 1985, 26, 705-708.
14. 3): δ 170.6 (s, Ac), 166.7 (s, C-15), 163.0 (s, C-13), 148.3 (s, C-8), 114.3 (d, C-14), 106.3 (t, C-17), 72.5 (d, C-2′), 61.4 (t, C-1′ or C-3′), 61.1 (t, C-3′ or C-1′), 56.2 (d, C-9), 55.5 (d, C-5), 42.1 (t, C-3), 40.0 (t, C-12), 39.7 (s, C-10), 39.1 (t, C-1), 38.3 (t, C-7), 33.6 (s, C-4), 33.6 (q, C-19), 24.4 (t, C-6), 21.7 (q, C-18), 21.5 (t, C-11), 21.1 (q, Ac), 19.4 (t, C-2), 19.1 (q, C-16), 14.5 (q, C-20). Numbering is according to Ref. 8.
15. 13C-NMR data are identical with those previously reported in ref. 6.
16. c 41.1 (t, C-4), 39.7 (t, C-8 and C-12), 26.8 (t, C-13), 26.4 (t, C-9), 26.0 (t, C-5), 25.7 (q, C-16), 21.0 (q, Ac), 19.1 (q, C-20), 17.7 (s, C-17), 16.0 (q, C-18 and C-19). Values with the same letter are interchangeable. Numbering is according to Ref. 18.
17. Vlad, P. F.; Ungur, N.D.; Nguen, V.T. Russian Chem. Bull. 1995, 44, 2404-2411.