Enantiospecific synthesis of (+)-(1S,2R,6S)-1,2-dimethylbicyclo[4.3.0]nonan-8-one and (-)-7-epibakkenolide-A
作者： A. Srikrishna , T. Jagadeeswar Reddy
DOI: 10.1016/S0040-4020(98)00672-3
关键词: Organic chemistry 、 Conjugate 、 Alkylation 、 Wacker process 、 Diketone 、 Ketone 、 Aldol condensation 、 Bicyclic molecule 、 Intramolecular force 、 Chemistry
摘要: Synthesis of the chiral bicyclic ketone mentioned in title starting from R-carvone, and its elaboration to 7-epibakkenolide-A is described. Conjugate addition dimethyl copperlithium R-carvone followed by alkylation intermediate enolate generated allylated compound 6, which was transformed into diketone 12 via a sequence reactions comprising regiospecific Wacker oxidation, ozonation-Criegee rearrangement as key reactions. Intramolecular aldol condensation catalytic hydrogenation converted (+)-3, optical antipode derived sesquiterpenes bakkenolide-A fukinone. A 5-exo-dig radical cyclisation based strategy 3 7-epibakkenolide-A.
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sci-hub.se 参考文章(28)
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
Benoît Hartmann, Alice M. Kanazawa, Jean-Pierre Deprés, Andrew E. Greene, Stereoselective synthesis of homogynolide-A, A bakkane from homogyne alpina Tetrahedron Letters. ,vol. 32, pp. 767- 768 ,(1991) , 10.1016/S0040-4039(00)74881-7
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+
Stuart L. Schreiber, Wai-Fong Liew, Criegee rearrangement of α-alkoxy hydroperoxides a synthesis of esters and lactones that complements the baeyer-villiger oxidation of ketones Tetrahedron Letters. ,vol. 24, pp. 2363- 2366 ,(1983) , 10.1016/S0040-4039(00)81926-7
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
Adusumilli Srikrishna, Sankuratri Nagaraju, Somepalli Venkateswarlu, A stereoselective synthesis of (±)-homogynolide-B Tetrahedron Letters. ,vol. 35, pp. 429- 432 ,(1994) , 10.1016/0040-4039(94)85072-0
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
Benoît Hartmann, Jean-Pierre Deprés, Andrew E. Greene, Marco E. Freire^de Lima, Stereoselective bakkane synthesis: (±)palmosalide C Tetrahedron Letters. ,vol. 34, pp. 1487- 1490 ,(1993) , 10.1016/S0040-4039(00)60325-8
J. Harmatha, Z. Samek, M. Synáčková, L. Novotný, V. Herout, F. Šorm, Neutral components of the extract from Homogine alpina (L.) CASS. Collection of Czechoslovak Chemical Communications. ,vol. 41, pp. 2047- 2058 ,(1976) , 10.1135/CCCC19762047