An enantioselective solutions towards synthesizing “skip” 1,3 dimethyl stereocenters. A synthesis of 4S(2E,4R∗,6R∗)-4,6-Dimethyl-2-octenoic acid

作者: Richard H. Schlessinger , Kevin W. Gillman

DOI: 10.1016/0040-4039(96)00015-9

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摘要: Abstract A versatile method of synthesizing “skip” 1,3 dimethyl stereocenters via an enantioselective aldol reaction followed by stereoselective catalytic hydrogenation produces three syn contiguous chiral centers. Barton deoxygenation the intermediary hydroxyl group provides desired skip array.

参考文章(9)
W.-D. Rudorf, A. D. Dunn, Carbon disulphide in organic chemistry Ellis Horwood , Halsted Press. ,(1988)
Kyriacos C. Nicolaou, Eddy W. Yue, Yoshimitsu Naniwa, Francesco De Riccardis, Alan Nadin, James E. Leresche, Susan La Greca, Zhen Yang, Zaragozic Acid A/Squalestatin S1: Synthetic and Retrosynthetic Studies Angewandte Chemie. ,vol. 33, pp. 2184- 2187 ,(1994) , 10.1002/ANIE.199421841
R. E. Bowman, K. D. Brunt, K. E. Godfrey, L. Kruszynska, A. A. Reynolds, R. I. Thrift, D. Waite, W. R. N. Williamson, Syntheses of flufenamic acid metabolites I and II and other N-aryl-anthranilic acids Journal of the Chemical Society, Perkin Transactions 1. ,vol. 1, pp. 1- 4 ,(1973) , 10.1039/P19730000001
Norman L. Allinger, Conformational analysis. 130. MM2. A hydrocarbon force field utilizing V1 and V2 torsional terms Journal of the American Chemical Society. ,vol. 99, pp. 8127- 8134 ,(1977) , 10.1021/JA00467A001
PHILIP J. SIDEBOTTOM, RONA M. HIGHCOCK, STEPHEN J. LANE, PAN A. PROCOPIOU, NIGEL S. WATSON, The squalestatins, novel inhibitors of squalene synthase produced by a species of Phoma. II. Structure elucidation. The Journal of Antibiotics. ,vol. 45, pp. 648- 658 ,(1992) , 10.7164/ANTIBIOTICS.45.648
Hiroyuki Ishiwata, Hiroki Sone, Hideo Kigoshi, Kiyoyuki Yamada, Total Synthesis of Doliculide, a Potent Cytotoxic Cyclodepsipeptide from the Japanese Sea Hare Dolabella auricularia Journal of Organic Chemistry. ,vol. 59, pp. 4712- 4713 ,(1994) , 10.1021/JO00096A003
Dinesh V. Patel, Frank. VanMiddlesworth, John. Donaubauer, Peter. Gannett, Charles J. Sih, Synthesis of the proposed penultimate biosynthetic triene intermediate of monensin A Journal of the American Chemical Society. ,vol. 108, pp. 4603- 4614 ,(1986) , 10.1021/JA00275A055
Yoshimitsu Nagao, Takehisa Inoue, Keiji Hashimoto, Yuichi Hagiwara, Masahito Ochiai, Eiichi Fujita, A facile chiral synthesis of (+)-Prelog–Djerassi lactonic acid methyl ester using five-membered heterocyclic chiral reagents Journal of The Chemical Society, Chemical Communications. pp. 1419- 1420 ,(1985) , 10.1039/C39850001419
David J. Hart, Kenichi Kanai, New approach to Lythraceae alkaloids: total synthesis of (.+-.)-vertaline Journal of Organic Chemistry. ,vol. 13, pp. 1555- 1560 ,(1982) , 10.1021/JO00347A036