Cycloaldol Approach to the Isobenzofuran Core of Eunicellin Diterpenes
作者： Yonghai Chai , David A. Vicic , Matthias C. McIntosh
DOI: 10.1021/OL034052F
关键词: Eunicellin 、 Stereochemistry 、 Methacrolein 、 Aldol reaction 、 Chemistry 、 Ring (chemistry) 、 Adduct 、 Yield (chemistry) 、 Isobenzofuran 、 Keto–enol tautomerism
摘要: A novel cycloaldol approach to the isobenzofuran core common many of eunicellin diterpenes is described. The precursor was prepared by aldol addition (S)-(+)-carvone and methacrolein followed etherification a glycolate ester. Chemoselective enolization ester led adduct in high yield diastereoselectivity. An oxidative rearrangement−allylic diazene rearrangement sequence established requisite cis ring fusion.
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sci-hub.se 参考文章(13)
Ravi S. Harapanhalli, Approach to the synthesis of side-chain eudesmanediols: synthesis of kudtriol from 1-(α)-santonin Journal of The Chemical Society-perkin Transactions 1. pp. 3149- 3154 ,(1988) , 10.1039/P19880003149
Sang-phyo Hong, Harriet A. Lindsay, Tripura Yaramasu, Xiaowei Zhang, Matthias C. McIntosh, Intramolecularly Competitive Ireland-Claisen Rearrangements: Scope and Potential Applications to Natural Product Synthesis Journal of Organic Chemistry. ,vol. 67, pp. 2042- 2055 ,(2002) , 10.1021/JO010752R
Ian Paterson, Alison N. Hulme, Total Synthesis of (-)-Ebelactone A and B Journal of Organic Chemistry. ,vol. 60, pp. 3288- 3300 ,(1995) , 10.1021/JO00116A010
Jeffrey A. Dodge, John I. Trujillo, Misti Presnell, Effect of the acidic component on the Mitsunobu inversion of a sterically hindered alcohol Journal of Organic Chemistry. ,vol. 59, pp. 234- 236 ,(1994) , 10.1021/JO00080A039
Charles M. Garner, Brett C. Mossman, Mark E. Prince, The epimerization of α-chiral hydrazones: Menthonetosylhydrazone Tetrahedron Letters. ,vol. 34, pp. 4273- 4276 ,(1993) , 10.1016/S0040-4039(00)79327-0
Steven D. Burke, William F. Fobare, Gregory J. Pacofsky, Chelation control of enolate geometry. Acyclic diastereoselection via the enolate Claisen rearrangement Journal of Organic Chemistry. ,vol. 48, pp. 5221- 5228 ,(1983) , 10.1021/JO00174A013
David W. C. MacMillan, Larry E. Overman, Enantioselective Total Synthesis of (-)-7-Deacetoxyalcyonin Acetate. First Synthesis of a Eunicellin Diterpene Journal of the American Chemical Society. ,vol. 117, pp. 10391- 10392 ,(1995) , 10.1021/JA00146A028
Stephen F. Martin, James B. White, Intramolecular photochemical [2+2] cycloadditions. Regiochemistry of the photocyclizations of some oxygen-substituted 6-allylcyclohexenones. Tetrahedron Letters. ,vol. 23, pp. 23- 26 ,(1982) , 10.1016/S0040-4039(00)97522-1
George Majetich, Stephen Condon, Kenneth Hull, Saeed Ahmad, 1,3-Oxidative rearrangements of dienols Tetrahedron Letters. ,vol. 30, pp. 1033- 1036 ,(1989) , 10.1016/S0040-4039(01)80351-8
Xavier Creary, Reactions of pivaloin derivatives with lithium tetramethylpiperidide Journal of Organic Chemistry. ,vol. 11, pp. 2419- 2425 ,(1980) , 10.1021/JO01300A031