Oxidative transformations of cembrane diterpenoids III. Epoxycembrenes
Article
First Online:
Summary
1. It has been established that the epoxidation of cembrene with perbenzoic and peracetic acids takes place stereospecifically at each of the trisubstituted double bonds with the formation of 4S,5R-, 7S,8S-, and 11S,12S-monoepoxycembrenes, the structures and absolute configurations of which have been established by spectral methods.
2. Epoxidation of cembrene at the C11–C12 double bonds under the conditions used takes place preferentially as compared with epoxidation at the C7–C8 double bond.
Keywords
Epoxide Diol Benzoyl Chloride Peracetic Acid Asymmetric CenterPreview
Unable to display preview. Download preview PDF.
Literature cited
- 1.A. J. Weinheimer, R. E. Middlebrook, J. O. Bledsoe, and W. E. Marsico, J. Chem. Soc., (D), 384 (1968).Google Scholar
- 2.M. B. Hossain and D. van der Helm, Rec. Trav. Chim.,88, 1413 (1969).CrossRefGoogle Scholar
- 3.J. P. Springer, J. Clardy, R. H. Cox, H. G. Gutler, and R. J. Cole, Tetrahedron Lett., 2737 (1975).Google Scholar
- 4.V. A. Raldugin, A. I. Rezvukhin, and V. A. Pentegova, Khim. Prirodn. Soedin., 598 (1971).Google Scholar
- 5.V. S. Joshi, N. P. Damodaran, and Sukh Dev., Tetrahedron,24, 5817 (1968).CrossRefGoogle Scholar
- 6.U. Nagai and H. Iga, Tetrahedron,26, 725 (1970).CrossRefGoogle Scholar
- 7.M. G. B. Drew, D. H. Templeton, and A. Zalkin, Acta Cryst.,25B, 261 (1969).CrossRefGoogle Scholar
- 8.V. A. Raldugin, V. K. Fedorov, and V. A. Penterova, Khim. Prirodn. Soedin., 391 (1976).Google Scholar
- 9.V. A. Raldugin, A. I. Rezvukhin, L. Ya. Korotkikh, and V. A. Pentegova, Khim. Prirodn. Soedin., 54 (1977).Google Scholar
- 10.F. J. Schmitz, D. J. Vanderah, and L. S. Ciereszko, J. Chem. Soc., D, 407 (1974).Google Scholar
- 11.G. Berti, F. Bottari, B. Macchia, and F. Macchia, Tetrahedron,21, 3277 (1965).CrossRefGoogle Scholar
- 12.F. P. Greenspan, J. Am. Chem. Soc.,68, 907 (1946).CrossRefGoogle Scholar
Copyright information
© Plenum Publishing Corporation 1978