Unprecedented grob-type fragmentation of 5-dioxolan-bicyclo[4.2.0]octan-2-ones into 3-(methoxycarbonylmethyl)cyclohexanones

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3469-3470

  De Giacomo, Marzia ^a   Bettolo, Rinaldo Marini ^a   Scarpelli, Rita ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; DITERPENE;

ARTICLE; DRUG DEGRADATION; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030919221     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00657-6     Document Type: Article

References (17)

1. -1, NMR in δ.
2. 3): 22.8, 24.3, 25.9, 29.5, 32.0, 35.4, 37.3, 38.5, 49.3, 64.0, 64.4, 70.0, 108.0, 206.1; colourless oil.
3. Obtained from the corresponding olefin as described for the preparation of 1d in ref.7.
4. 3): 20.5, 25.8, 27.3, 28.3, 32.7, 37.0, 39.6, 41.0, 44.5, 51.1, 52.7, 172.1, 210.8; low melting oil (38-39°C).
5. A. Bartoletti, M. Berettoni, F. Catteruccia, G. De Chiara, R. Marini Bettolo, C. Mastrangeli, R. Scarpelli, C. Tozzi, D. Lamba, Gazz. Chim. Ital., 1996, 126, 223.
6. 2O): 99.5-100.6°C.
7. Derived from (-)-abietic acid; M. Berettoni, G. De Chiara, T. Iacoangeli, P. Lo Surdo, R. Marini Bettolo, L. Montagnini di Mirabello, L. Nicolini, R. Scarpelli, Helv. Chim. Acta, 1996, 79, 2035.
8. 4): 1734, 1711, as epimeric mixture at C(9).
9. 3): 15.8, 18.3, 21.4, 21.7, 28.3, 28.6, 29.5, 30.1, 32.9, 33.0, 34.0, 34.3, 37.9, 40.3, 41.5, 41.9, 44.2, 45.3, 47.3, 173.7, 211.8; colourless oil.
10. 2O): 136.8-137.1°C.
11. a) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983, p. 273;
12. b) C.A. Grob, Angew. Chem. Int. Ed. Engl. 1969, 8, 535;
13. c) Fragmentation Reactions, P. Weyerstahl and H. Marschall in Comprehensive Organic Synthesis, Ed.-in-Chief B.M. Trost, Vol. Ed. E. Winterfeldt, vol. 6, Pergamon Press, Oxford, 1991, p. 1041.
14. a) E.J. Corey, R.L. Danheiser, S. Chandrasekaran, J. Org. Chem., 1976, 41, 260;
15. b) J.L. Namy, J. Souppe, H.B. Kagan, Tetrahedron Lett., 1983, 24, 765;
16. c) G.A. Molander, C.J. Kenny, J. Org. Chem., 1988, 53, 2132.
17. Natural Products Chemistry, eds. K. Nakanishi, T. Goto, S. Itô, S. Natori, S. Nozoe, vol. 1, Academic Press, Inc., New York, 1974, p. 255.