Structure determination, correction, and disproof of marine macrolide natural products by chemical synthesis

作者: Haruhiko Fuwa

DOI: 10.1039/D1QO00481F

关键词: Nuclear magnetic resonance spectroscopyStructure analysisChemistryLobatamide CPolyketideCallyspongiolideChemical synthesisComputational chemistry

摘要: Despite significant advances in NMR spectroscopy, structure elucidation of natural products, especially stereochemically complex polyketides with limited availability, is still a challenging task for chemists. Recent examples determination, correction and disproof structurally marine polyketide macrolides by chemical synthesis, namely lobatamide C, reidispongiolide A, callyspongiolide, palmerolide muironolide iriomoteolide-2a, chagosensine cases, are summarized this review, which highlights the scope limitation current NMR-based analysis vital role synthesis elucidation.

参考文章(189)
Hye-Dong Yoo, Sang-Jip Nam, Young-Won Chin, Min-Sun Kim, Misassigned natural products and their revised structures Archives of Pharmacal Research. ,vol. 39, pp. 143- 153 ,(2016) , 10.1007/S12272-015-0649-9
Kyle Young, Qing Xiao, Armen Zakarian, Toward the Synthesis of Muironolide A: Synthesis and Structure of Heteroleptic Lanthanide–Terpyridine Complexes with 2-Oxo Amides European Journal of Organic Chemistry. ,vol. 2015, pp. 2337- 2341 ,(2015) , 10.1002/EJOC.201500174
Scott E. Schaus, Bridget D. Brandes, Jay F. Larrow, Makoto Tokunaga, Karl B. Hansen, Alexandra E. Gould, Michael E. Furrow, Eric N. Jacobsen, Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)CoIII Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols Journal of the American Chemical Society. ,vol. 124, pp. 1307- 1315 ,(2002) , 10.1021/JA016737L
Ian Paterson, Kate Ashton, Robert Britton, Giuseppe Cecere, Gaëlle Chouraqui, Gordon J. Florence, Henner Knust, Jonathan Stafford, Total Synthesis of (−)‐Reidispongiolide A, an Actin‐Targeting Macrolide Isolated from the Marine Sponge Reidispongia coerulea Chemistry-an Asian Journal. ,vol. 3, pp. 367- 387 ,(2008) , 10.1002/ASIA.200700357
W.Clark Still, Cesare Gennari, Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination. Tetrahedron Letters. ,vol. 24, pp. 4405- 4408 ,(1983) , 10.1016/S0040-4039(00)85909-2
Hideo Kigoshi, Ichiro Hayakawa, Marine cytotoxic macrolides haterumalides and biselides, and related natural products Chemical Record. ,vol. 7, pp. 254- 264 ,(2007) , 10.1002/TCR.20119
William H. Gerwick, Bradley S. Moore, Lessons from the Past and Charting the Future of Marine Natural Products Drug Discovery and Chemical Biology Chemistry & Biology. ,vol. 19, pp. 85- 98 ,(2012) , 10.1016/J.CHEMBIOL.2011.12.014
Qing Xiao, Kyle Young, Armen Zakarian, Total Synthesis and Structural Revision of (+)-Muironolide A Journal of the American Chemical Society. ,vol. 137, pp. 5907- 5910 ,(2015) , 10.1021/JACS.5B03531