Total synthesis of balanol, part 2. Completion of the synthesis and investigation of the structure and reactivity of two key heterocyclic intermediates
作者： David Tanner , Lars Tedenborg , Antonio Almario , Ingrid Pettersson , Ingeborg Csöregh
DOI: 10.1016/S0040-4020(97)00167-1
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摘要: Abstract A convergent enantioselective total synthesis of the natural product (-)-balanol (1) is described. In addition to benzophenone fragment 8, key intermediates are chiral bicyclic aziridine 3 and corresponding epoxide 4, both which undergo highly regio- stereoselective nucleophilic ring-opening reactions, allowing control two stereogenic centres target molecule. The structure reactivity 4 have been investigated in some detail.
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M. Nardelli, Parst: A system of fortran routines for calculating molecular structure parameters from results of crystal structure analyses Computational Biology and Chemistry. ,vol. 7, pp. 95- 98 ,(1983) , 10.1016/0097-8485(83)85001-3
Teruaki Mukaiyama, New Synthetic Reactions Based on the Onium Salts of Aza‐Arenes [New synthetic methods (29)] Angewandte Chemie. ,vol. 18, pp. 707- 721 ,(1979) , 10.1002/ANIE.197907073
Paolo Crotti, Valeria Di Bussolo, Lucilla Favero, Mauro Pineschi, Regiochemical control of the ring opening of aziridines by means of chelating processes. 2. Synthesis and ring-opening reactions of aziridines derived from 5,6-dihydro-2H-pyran and of the diastereoisomeric cis- and trans-aziridines derived from 3-(benzyloxy)cyclohexene, 2-(benzyloxy)-3,6-dihydro-, and 2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran Tetrahedron. ,vol. 53, pp. 1417- 1438 ,(1997) , 10.1016/S0040-4020(96)01054-X
Paul G. Gassman, Thomas L. Guggenheim, Opening of epoxides with trimethylsilyl cyanide to produce .beta.-hydroxy isonitriles. A general synthesis of oxazolines and .beta.-amino alcohols Journal of the American Chemical Society. ,vol. 104, pp. 5849- 5850 ,(1982) , 10.1021/JA00385A078
M. Elise Tran Huu Dau, Robert H. Dodd, Philippe Dauban, Laurent Dubois, Reactivity of 2,3-Aziridino-2,3-dideoxy-D-lyxono-.gamma.-lactone Derivatives, Rigid Analogs of Aziridine-2-carboxylic Esters, toward Soft and Hard Nucleophiles: Control of Lactone vs Aziridine Ring Opening and C-2 vs C-3 Regioselectivity Journal of Organic Chemistry. ,vol. 60, pp. 2035- 2043 ,(1995) , 10.1021/JO00112A027
Inga Hoppe, Dieter Hoppe, Christian Wolff, Ernst Egert, Regine Herbst, 3‐Arylsulfonyloxazolidine als chirale Template; asymmetrische Synthese von 2‐substituierten 2‐Hydroxycyclohexancarbaldehyden aus 2‐Hydroxymethylencyclohexanon Angewandte Chemie. ,vol. 101, pp. 65- 67 ,(1989) , 10.1002/ANGE.19891010115
Palaniappan Kulanthaivel, Yali F. Hallock, Christie Boros, Sean M. Hamilton, William P. Janzen, Lawrence M. Ballas, Carson R. Loomis, Jack B. Jiang, Barry Katz, Balanol: a novel and potent inhibitor of protein kinase C from the fungus Verticillium balanoides Journal of the American Chemical Society. ,vol. 115, pp. 6452- 6453 ,(1993) , 10.1021/JA00067A087
Paul G. Gassman, Robert S. Gremban, Directive effects in the opening of epoxides with trimethylsilyl cyanide - zinc iodide. The establishment of three contiguous chiral centers. Tetrahedron Letters. ,vol. 25, pp. 3259- 3262 ,(1984) , 10.1016/S0040-4039(01)81357-5
John W. Lampe, Philip F. Hughes, Christopher K. Biggers, Shelley H. Smith, Hong Hu, Total Synthesis of (−)- and (+)-Balanol1 Journal of Organic Chemistry. ,vol. 61, pp. 4572- 4581 ,(1996) , 10.1021/JO952280K
Gordon S. Bates, Michael A. Varelas, A mild, general preparation of N-acyl aziridines and 2-substituted 4(S)-benzyloxazolines Canadian Journal of Chemistry. ,vol. 58, pp. 2562- 2566 ,(1980) , 10.1139/V80-408