Convergent Strategy Towards the Synthesis of Restricted Analogues of Peloruside A

作者: Nicolas Zimmermann , Pierre Pinard , Bertrand Carboni , Pascal Gosselin , Catherine Gaulon-Nourry

DOI: 10.1002/EJOC.201201728

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摘要: A rapid convergent strategy to access unsaturated analogues of peloruside has been demonstrated. This is depicted as an original C11-C12 aldol connection between a C12-C20 ketone fragment and C2-C11 pyran bearing aldehyde function, with high yield good level diastereoselectivity. The desired macrocycle was obtained by late-stage ring closing metathesis reaction.

参考文章(40)
West Lm, Bäckström Bt, Hood Ka, Northcote Pt, Berridge Mv, Miller Jh, The novel cytotoxic sponge metabolite peloruside A, structurally similar to bryostatin-1, has unique bioactivity independent of protein kinase C. Anti-cancer Drug Design. ,vol. 16, pp. 155- 166 ,(2001)
Masahiro Nomura, Takahiro Tanase, Tomohiro Ide, Masaki Tsunoda, Masahiro Suzuki, Hideharu Uchiki, Koji Murakami, Hiroyuki Miyachi, Design, Synthesis, and Evaluation of Substituted Phenylpropanoic Acid Derivatives as Human Peroxisome Proliferator Activated Receptor Activators. Discovery of Potent and Human Peroxisome Proliferator Activated Receptor α Subtype-Selective Activators Journal of Medicinal Chemistry. ,vol. 46, pp. 3581- 3599 ,(2003) , 10.1021/JM0205144
Amos B. Smith, Jason M. Cox, Noriyuki Furuichi, Craig S. Kenesky, Junying Zheng, Onur Atasoylu, William M. Wuest, Total synthesis of (-)-2-epi-peloruside A. Organic Letters. ,vol. 10, pp. 5501- 5504 ,(2008) , 10.1021/OL8019132
Zhiming Zhao, Richard E. Taylor, Rapid access to conformational analogues of (+)-peloruside A. Organic Letters. ,vol. 14, pp. 669- 671 ,(2012) , 10.1021/OL203268T
David A. Evans, Paul J. Coleman, Bernard Côté, 1,5-Asymmetric Induction in Methyl Ketone Aldol Addition Reactions Journal of Organic Chemistry. ,vol. 62, pp. 788- 789 ,(1997) , 10.1021/JO962417M
Meizhong Jin, Richard E. Taylor, Total Synthesis of (+)-Peloruside A Organic Letters. ,vol. 7, pp. 1303- 1305 ,(2005) , 10.1021/OL050070G
Lyndon M. West, Peter T. Northcote, Chris N. Battershill, Peloruside A:  A Potent Cytotoxic Macrolide Isolated from the New Zealand Marine SpongeMycalesp. The Journal of Organic Chemistry. ,vol. 65, pp. 445- 449 ,(2000) , 10.1021/JO991296Y
Richard E. Taylor, Meizhong Jin, Toward a total synthesis of peloruside A: enantioselective preparation of the C8-C19 region. Organic Letters. ,vol. 5, pp. 4959- 4961 ,(2003) , 10.1021/OL0358814
Tetsuji Harabe, Takatoshi Matsumoto, Takayuki Shioiri, Esters of 2,5-multisubstituted-1,3-dioxane-2-carboxylic acid: their conformational analysis and selective hydrolysis Tetrahedron. ,vol. 65, pp. 4044- 4052 ,(2009) , 10.1016/J.TET.2009.02.076