A direct route to angularly substituted hydrindanes. Formal synthesis of bakkenolide-A and synthesis of an advanced intermediate to umbellactal

作者: Soumitra Maity , Subrata Ghosh

DOI: 10.1016/J.TET.2009.09.029

关键词:

摘要: A direct route for the synthesis of highly functionalized angularly substituted hydrindanes has been developed. The key step involves RO-RCM an appropriately norbornene derivative. hydrindane derivative obtained in this way used to accomplish a formal bakkenolide-A. This protocol also extended advanced intermediate diterpene umbellactal.

参考文章(55)
K. Shirahata, T. Kato, Y. Kitahara, N. Abe, Constituents of genus petasites—IV Tetrahedron. ,vol. 25, pp. 3179- 3191 ,(1969) , 10.1016/S0040-4020(01)82850-7
Keizo Naya, Mitsuo Hayashi, Ichiro Takagi, Seisuke Nakamura, Masakazu Kobayashi, The Structural Elucidation of Sesquiterpene Lactones fromPetasites japonicusMaxim Bulletin of the Chemical Society of Japan. ,vol. 45, pp. 3673- 3685 ,(1972) , 10.1246/BCSJ.45.3673
Olivier Hamelin, Jean-Pierre Deprés, Andrew E. Greene, Bernard Tinant, Jean-Paul Declercq, Highly Stereoselective First Synthesis of an A-Ring-Functionalized Bakkane: Novel Free-Radical Approach to 9-Acetoxyfukinanolide Journal of the American Chemical Society. ,vol. 118, pp. 9992- 9993 ,(1996) , 10.1021/JA962517+
Amy C. Hart, Andrew J. Phillips, Total synthesis of (+)-cylindramide A. Journal of the American Chemical Society. ,vol. 128, pp. 1094- 1095 ,(2006) , 10.1021/JA057899A
Aaron Wrobleski, Kiran Sahasrabudhe, Jeffrey Aubé, Asymmetric Total Synthesis of Dendrobatid Alkaloids: Preparation of Indolizidine 251F and Its 3-Desmethyl Analogue Using an Intramolecular Schmidt Reaction Strategy Journal of the American Chemical Society. ,vol. 126, pp. 5475- 5481 ,(2004) , 10.1021/JA0320018
J. Nawrot, Elzbieta Błoszyk, J. Harmatha, L. Novotný, The effect of bisaboloangelone, helenalin and bakkenolide A on development and behaviour of some stored product beetles Zeitschrift für Angewandte Entomologie. ,vol. 98, pp. 394- 398 ,(2009) , 10.1111/J.1439-0418.1984.TB02727.X
Mauricio G. Constantino, Kleber T. de Oliveira, Ellen C. Polo, Gil V. J. da Silva, Timothy J. Brocksom, Core Structure of Eremophilanes and Bakkanes through Niobium Catalyzed Diels−Alder Reaction: Synthesis of (±)-Bakkenolide A Journal of Organic Chemistry. ,vol. 71, pp. 9880- 9883 ,(2006) , 10.1021/JO061722X