The synthetic challenge of diazonamide A, a macrocyclic indole bis-oxazole marine natural product

作者: Mathilde Lachia , Christopher J. Moody

DOI: 10.1039/B705663J

关键词: Indole testAminalCombinatorial chemistryBiologyOxazoleNatural productOrganic chemistry

摘要: Covering: 1991 to August 2007 The complex structure of the marine metabolite diazonamide A comprises a dichlorinated indole bis-oxazole heteroaromatic fragment, and [b]-fused dihydrobenzofuran–dihydroindole unit containing an aminal carbon, all incorporated within strained double macrocyclic array. This review details synthetic studies on this fascinating natural product starting from early original (1991–2001), through synthesis originally proposed subsequent structural revision, eventual successful syntheses itself. Throughout we focus innovative ways in which chemists have approached challenges posed by product.

参考文章(80)
Ulrich Schöllkopf, Rolf Schröder, 2‐Unsubstituted Oxazoles from α‐Metalated Isocyanides and Acylating Agents Angewandte Chemie. ,vol. 10, pp. 333- 333 ,(1971) , 10.1002/ANIE.197103331
Christopher J. Moody, Mark C. Bagley, Total synthesis of (+)-nostocyclamide 1 Journal of The Chemical Society-perkin Transactions 1. pp. 601- 608 ,(1998) , 10.1039/A704094F
Chi-Ming Cheung, Frederick W. Goldberg, Philip Magnus, Claire J. Russell, Rachel Turnbull, Vince Lynch, An expedient formal total synthesis of (-)-diazonamide A via a powerful, stereoselective O-aryl to C-aryl migration to form the C10 quaternary center. Journal of the American Chemical Society. ,vol. 129, pp. 12320- 12327 ,(2007) , 10.1021/JA0744448
N. S. Williams, A. W. G. Burgett, A. S. Atkins, X. Wang, P. G. Harran, S. L. McKnight, Therapeutic anticancer efficacy of a synthetic diazonamide analog in the absence of overt toxicity Proceedings of the National Academy of Sciences of the United States of America. ,vol. 104, pp. 2074- 2079 ,(2007) , 10.1073/PNAS.0611340104
Armin Walser, John F. Blount, R. Ian Fryer, Synthesis and transformations of some 3-chloro- and 3-nitroindolenines Journal of Organic Chemistry. ,vol. 38, pp. 3077- 3084 ,(1973) , 10.1021/JO00958A001
Peter Wipf, Chris P. Miller, A new synthesis of highly functionalized oxazoles Journal of Organic Chemistry. ,vol. 58, pp. 3604- 3606 ,(1993) , 10.1021/JO00066A004
Daniela Schley, Alexander Radspieler, Guido Christoph, Jürgen Liebscher, α-Arylation of 2-Arylacetates and Benzofuran-2-one with Tricarbonyl(fluoroarene)chromium Complexes European Journal of Organic Chemistry. ,vol. 2002, pp. 369- 374 ,(2002) , 10.1002/1099-0690(20021)2002:2<369::AID-EJOC369>3.0.CO;2-7