Total Synthesis and Stereochemical Assignment of (±)-Sorbiterrin A

Abstract

A concise, biomimetic approach to sorbiterrin A has been developed employing consecutive Michael additions of a 4-hydroxypyrone to a sorbicillinol derivative and silver nanoparticle-mediated bridged aldol/dehydration to construct the [3.3.1] ring system. The relative stereochemistry of sorbiterrin A was unambiguously confirmed by X-ray crystallographic analysis.

References

Page 1

	Year	Citations
Silver nanoparticle catalysed redox reaction: An electron relay effect Kaushik Mallick, Mike J. Witcomb Materials Chemistry and Physics EngineeringMetal NanoparticlesNanomaterialsPlasmonic CatalysisSilver Nanoparticle	2005	288
Organocatalytic Asymmetric Michael Reaction of Cyclic 1,3‐Dicarbonyl Compounds and α,β‐Unsaturated Ketones—A Highly Atom‐Economic Catalytic One‐Step Formation of Optically Active Warfarin Anticoagulant Nis Halland, Tore Hansen, Karl Anker Jørgensen Angewandte Chemie International Edition Racemic WarfarinEngineeringOrganic ChemistryChemistryMedicinal Chemistry	2003	263
Lewis base catalysis of bromo- and iodolactonization, and cycloetherification Scott E. Denmark, Matthew T. Burk Proceedings of the National Academy of Sciences Chemical EngineeringNovel OrganocatalystsEngineeringHeterocyclicCyclization Selectivity	2010	251
Direct β-Functionalization of Cyclic Ketones with Aryl Ketones via the Merger of Photoredox and Organocatalysis Filip Petronijević, Manuel Nappi, David W. C. MacMillan Journal of the American Chemical Society	2013	213
Hypervalent iodine oxidation of N-acyltyramines: synthesis of quinol ethers, spirohexadienones, and hexahydroindol-6-ones Yasuyuki Kita, Hirofumi Tohma, Kazumi Kikuchi, The Journal of Organic Chemistry HalogenationChemical EngineeringEnantioselective SynthesisEngineeringHeterocyclic	1991	171
Silver Nanoparticle-Catalyzed Diels−Alder Cycloadditions of 2′-Hydroxychalcones Huan Cong, Clinton F. Becker, Sean J. Elliott, Journal of the American Chemical Society	2010	149
Catalytic Asymmetric Total Synthesis of <i>ent</i>‐Hyperforin Y. Shimizu, Shi‐Liang Shi, Hiroyuki Usuda, Angewandte Chemie International Edition	2010	145
Chiral Squaramides as Highly Enantioselective Catalysts for Michael Addition Reactions of 4‐Hydroxycoumarins and 4‐Hydroxypyrone to β,γ‐Unsaturated α‐Keto Esters Dan‐Qian Xu, Yi‐Feng Wang, Wei Zhang, Chemistry - A European Journal	2010	138
Separation and identification of DMPO adducts of oxygen-centered radicals formed from organic hydroperoxides by HPLC-ESR, ESI-MS and MS/MS Qiong Guo, Steven Y. Qian, Ronald P. Mason Journal of the American Society for Mass Spectrometry Radical EmissionLipid PeroxidationMagnetic ResonanceMolecular BiologyCumene Hydroperoxide	2003	135
Biomimetic Total Synthesis of Bisorbicillinol, Bisorbibutenolide, Trichodimerol, and Designed Analogues of the Bisorbicillinoids K. C. Nicolaou, Georgios Vassilikogiannakis, Klaus B. Simonsen, Journal of the American Chemical Society Bioorganic ChemistryEngineeringNovel Dimerization ReactionsOrganic ChemistryHeterocycle Chemistry	2000	126

Page 1