Strategies for the synthesis of the novel antitumor agent peloruside A.
作者： David R Williams , Nicolas Zorn , Partha P Nag
DOI:
关键词: Chemistry 、 Structure–activity relationship 、 Bridged Bicyclo Compounds 、 Stereochemistry 、 Peloruside A 、 Antitumor activity 、 Cancer 、 Combinatorial chemistry
摘要: The microtubule-stabilizing agent (+)-peloruside A has emerged as a potential therapeutic for the treatment of cancer. Two total syntheses have been published and these reports stimulated additional studies to advance methodology strategies accessing this molecular architecture. This review details biological data, modeling conformation analyses, synthetic toward synthesis A, that were reported prior December 2007.
参考文章(33)
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)
Peter T. Northcote, St. John Wakefield, Michael V. Berridge, John H. Miller, Lyndon M. West, Berber Rouwé, Kylie A. Hood, Peloruside A, a Novel Antimitotic Agent with Paclitaxel-like Microtubule- stabilizing Activity Cancer Research. ,vol. 62, pp. 3356- 3360 ,(2002)
Darren W. Engers, Martin J. Bassindale, Brian L. Pagenkopf, Synthesis of the C(1)−C(12) Segment of Peloruside A by an α-Benzyloxymethyl Ketone Aldol Strategy Organic Letters. ,vol. 6, pp. 663- 666 ,(2004) , 10.1021/OL036393Z
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
Emmanuel Roulland, Mikhail S. Ermolenko, Synthesis of the C12-C19 fragment of (+)-peloruside A through a diastereomer-discriminating RCM reaction. Organic Letters. ,vol. 7, pp. 2225- 2228 ,(2005) , 10.1021/OL050588K
A. Ding, F Porteu, E Sanchez, C. Nathan, Shared actions of endotoxin and taxol on TNF receptors and TNF release Science. ,vol. 248, pp. 370- 372 ,(1990) , 10.1126/SCIENCE.1970196
Oriol Pineda, Jaume Farràs, Laura Maccari, Fabrizio Manetti, Maurizio Botta, Jaume Vilarrasa, Computational comparison of microtubule-stabilising agents laulimalide and peloruside with taxol and colchicine. Bioorganic & Medicinal Chemistry Letters. ,vol. 14, pp. 4825- 4829 ,(2004) , 10.1016/J.BMCL.2004.07.053
Kandasamy Sakthivel, Wolfgang Notz, Tommy Bui, Carlos F. Barbas, Amino Acid Catalyzed Direct Asymmetric Aldol Reactions: A Bioorganic Approach to Catalytic Asymmetric Carbon-Carbon Bond-Forming Reactions Journal of the American Chemical Society. ,vol. 123, pp. 5260- 5267 ,(2001) , 10.1021/JA010037Z