A convenient route to 1-(2-oxiranyl)-1,4-diketones and their application to the synthesis of endo-brevicomin, endo-isobrevicomin, frontalin and related compounds via alkylated 6,8-dioxabicyclo[3.2.1]octan-2-ones
作者： Vladimir I Tyvorskii , Dmitry A Astashko , Oleg G Kulinkovich , None
DOI: 10.1016/J.TET.2003.12.027
关键词:
摘要: Abstract 1-(2-Oxiranyl)-1,4-alkanediones were prepared from the ethylene acetals of ethyl 4-oxoalkanoates via oxidation intermediate 1,2-dialkylcyclopropanols having a protected carbonyl group in an aliphatic chain. Intramolecular acetalization these epoxy dicarbonyl compounds gave alkylated 6,8-dioxabicyclo[3.2.1]octan-2-ones good yields. The latter found suitable to be precursors for (±)-endo-brevicomin and its 2-hydroxy derivative, as well (±)-endo-isobrevicomin (±)-frontalin.
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sci-hub.se 参考文章(36)
T. H. Chan, L. M. Chen, D. Wang, L. H. Li, Enantioselective synthesis of epoxides via Sharpless epoxidation of alkenylsilanols Canadian Journal of Chemistry. ,vol. 71, pp. 60- 67 ,(1993) , 10.1139/V93-009
Robert Chênevert, Dave Caron, Chemoenzymatic enantioselective synthesis of (1S,5R)-(−)-frontalin Tetrahedron: Asymmetry. ,vol. 13, pp. 339- 342 ,(2002) , 10.1016/S0957-4166(02)00085-X
Benjamin List, Doron Shabat, Carlos F. Barbas III, Richard A. Lerner, Enantioselective Total Synthesis of Some Brevicomins Using Aldolase Antibody 38C2 Chemistry: A European Journal. ,vol. 4, pp. 881- 885 ,(1998) , 10.1002/(SICI)1521-3765(19980515)4:5<881::AID-CHEM881>3.0.CO;2-#
Regina Mikie Kanada, Takahiko Taniguchi, Kunio Ogasawara, Asymmetric hydrogen transfer protocol for a synthesis of (+)-frontalin and (−)-malyngolide Tetrahedron Letters. ,vol. 41, pp. 3631- 3635 ,(2000) , 10.1016/S0040-4039(00)00430-5
Oleg G. Kulinkovich, The chemistry of cyclopropanols Chemical Reviews. ,vol. 103, pp. 2597- 2632 ,(2003) , 10.1021/CR010012I
Ernst Weitz, Alfred Scheffer, Über die Einwirkung von alkalischem Wasserstoffsuperoxyd auf ungesättigte Verbindungen European Journal of Inorganic Chemistry. ,vol. 54, pp. 2327- 2344 ,(1921) , 10.1002/CBER.19210540922
Allan C. Oehlschlager, Blair D. Johnston, Synthesis of the enantiomers of endo-brevicomin Journal of Organic Chemistry. ,vol. 52, pp. 940- 943 ,(1987) , 10.1021/JO00381A044
John K. Gallos, Loukia C. Kyradjoglou, Theocharis V. Koftis, A Concise Synthesis of (-)-endo-Brevicomin HETEROCYCLES. ,vol. 55, pp. 781- 784 ,(2001) , 10.3987/COM-01-9161
I. G. Tishchenko, O. G. Kulinkovich, N. V. Masalov, N,N-Dialkyl-4-oxoalkanamides fromgem-Dichlorocyclopropyl Ketones Synthesis. ,vol. 1982, pp. 268- 270 ,(1982) , 10.1055/S-1982-29773
Oleg G. Kulinkovich, Armin de Meijere, 1,n-Dicarbanionic Titanium Intermediates from Monocarbanionic Organometallics and Their Application in Organic Synthesis Chemical Reviews. ,vol. 100, pp. 2789- 2834 ,(2000) , 10.1021/CR980046Z