Stereoselective total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (−)-(6S,2′S)-epi cryptocaryalactone via asymmetric acetate aldol reaction
作者： J.S. Yadav , Dinesh C. Bhunia , B. Ganganna
DOI: 10.1016/J.TETLET.2012.02.073
关键词: Aldol reaction 、 Chemistry 、 Total synthesis 、 Stereoselectivity 、 Acetal 、 Intramolecular force 、 Stereochemistry
摘要: Abstract The total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (−)-(6S,2′S)-epi cryptocaryalactone is reported based on asymmetric acetate aldol reaction. Still–Gennari reaction, Evans acetal intramolecular oxa-Michael reaction lactonisation are the key steps in target synthesis.
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Gowravaram Sabitha, V. Bhaskar, S. Siva Sankara Reddy, J.S. Yadav, Stereoselective total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (−)-(6S,2′S)-epi cryptocaryalactone Tetrahedron. ,vol. 64, pp. 10207- 10213 ,(2008) , 10.1016/J.TET.2008.08.032
Xin-Ping Fang, Jon E. Anderson, Ching-Jer Chang, Jerry L. McLaughlin, Phillip E. Fanwick, Two new styryl lactones, 9-deoxygoniopypyrone and 7-epi-goniofufurone, from Goniothalamus giganteus. Journal of Natural Products. ,vol. 54, pp. 1034- 1043 ,(1991) , 10.1021/NP50076A017
W.Clark Still, Cesare Gennari, Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination. Tetrahedron Letters. ,vol. 24, pp. 4405- 4408 ,(1983) , 10.1016/S0040-4039(00)85909-2
Guillermo Schmeda-Hirschmann, Luis Astudillo, Jaume Bastida, Carles Codina, Antonieta Rojas De Arias, María Elena Ferreira, Alba Inchaustti, Gloria Yaluff, Cryptofolione derivatives from Cryptocarya alba fruits. Journal of Pharmacy and Pharmacology. ,vol. 53, pp. 563- 567 ,(2010) , 10.1211/0022357011775686
Christopher M. Sturgeon, Bruno Cinel, Ana R. Díaz-Marrero, Lianne M. McHardy, Michelle Ngo, Raymond J. Andersen, Michel Roberge, Abrogation of ionizing radiation-induced G2 checkpoint and inhibition of nuclear export by Cryptocarya pyrones. Cancer Chemotherapy and Pharmacology. ,vol. 61, pp. 407- 413 ,(2008) , 10.1007/S00280-007-0483-Y
Yuji MORI, Hiroshi FURUKAWA, Synthesis of Cryptocaryalactone, a 1, 3-Polyol-Derived Unsaturated Lactone Chemical & Pharmaceutical Bulletin. ,vol. 42, pp. 2161- 2163 ,(1994) , 10.1248/CPB.42.2161
K. Jewers, J.B. Davis, J. Dougan, A.H. Manchanda, G. Blunden, Aye Kyi, S. Wetchapinan, Goniothalamin and its distribution in four Goniothalamus species Phytochemistry. ,vol. 11, pp. 2025- 2030 ,(1972) , 10.1016/S0031-9422(00)90168-7
Jhillu Yadav, Veerjala Kumar, Ramisetti Rao, Pabbaraja Srihari, A Concise Stereoselective Total Synthesis of Herbarumin III Synthesis. ,vol. 2008, pp. 1938- 1942 ,(2008) , 10.1055/S-2008-1067089
Jean-Marc Nuzillard, Ahcene Boumendjel, Georges Massiot, A new synthesis of α,β-unsaturated aldehydes Tetrahedron Letters. ,vol. 30, pp. 3779- 3780 ,(1989) , 10.1016/S0040-4039(01)80653-5
Pablo Etayo, Ramón Badorrey, María D. Díaz-de-Villegas, José A. Gálvez, Base-controlled diastereodivergent synthesis of (R)- and (S)-2-substituted-4-alkylidenepiperidines by the Wadsworth-Emmons reaction. Journal of Organic Chemistry. ,vol. 72, pp. 1005- 1008 ,(2007) , 10.1021/JO062075C