Cyclopentaannulation of allyl alcohols via a radical cyclisation reaction. Total synthesis of 4-epibakkenolide-A

作者: A. Srikrishna , R. Viswajanani , J. A. Sattigeri

DOI: 10.1039/C39950000469

关键词:

摘要: A four step cyclopentaannulation methodology starting from allyl alcohols using 5-exo-trig radical cyclisation as the key reaction, and its application to total synthesis of 4-epibakkenolide is described.

参考文章(12)
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
A. Srikrishna, G. Sundarababu, A radical cyclisation reaction based strategy to 2,3,5-tri- and tetrasubstituted furans Tetrahedron. ,vol. 46, pp. 7901- 7910 ,(1990) , 10.1016/S0040-4020(01)90088-2
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
Adusumilli Srikrishna, T. Jagadeeswar Reddy, Sankuratri Nagaraju, Jitendra A. Sattigeri, A stereoselective total synthesis of bakkenolide-A (fukinanolide) Tetrahedron Letters. ,vol. 35, pp. 7841- 7844 ,(1994) , 10.1016/0040-4039(94)80132-0
Masaaki Miyashita, Tetsuji Yanami, Akira Yoshikoshi, New 1,4-diketone synthesis using nitroolefins and trimethylsilyl enol ethers. A convenient regiospecific route to cyclopentenones Journal of the American Chemical Society. ,vol. 98, pp. 4679- 4681 ,(1976) , 10.1021/JA00431A074
K. Shirahata, T. Kato, Y. Kitahara, N. Abe, Mass spectra of bakkenolides and their derivatives Tetrahedron. ,vol. 25, pp. 4671- 4680 ,(1969) , 10.1016/S0040-4020(01)83011-8
Gilbert. Stork, Philip Michael. Sher, A catalytic tin system for trapping of radicals from cyclization reactions. Regio- and stereocontrolled formation of two adjacent chiral centers Journal of the American Chemical Society. ,vol. 108, pp. 303- 304 ,(1986) , 10.1021/JA00262A024
Goverdhan Mehta, Srinivas Rao Karra, An expedient cyclopentenone annulation protocol Tetrahedron Letters. ,vol. 32, pp. 3215- 3216 ,(1991) , 10.1016/S0040-4039(00)79726-7
Craig P. Jasperse, Dennis P. Curran, Thomas L. Fevig, Radical reactions in natural product synthesis Chemical Reviews. ,vol. 91, pp. 1237- 1286 ,(1991) , 10.1021/CR00006A006
Muthyala Ramaiah, Radical reactions in organic synthesis Tetrahedron. ,vol. 43, pp. 3541- 3676 ,(1987) , 10.1016/S0040-4020(01)86853-8