Topic
Dieckmann condensation
About: Dieckmann condensation is a research topic. Over the lifetime, 269 publications have been published within this topic receiving 2728 citations.
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TL;DR: A concise (nine-step) and effective (19% overall yield) total synthesis of ningalin D is disclosed and is based on a key 1,2,4,5-tetrazine -->1,2-diazine --> pyrrole Diels-Alder strategy to assemble a fully substituted pyr role core central to its structure.
Abstract: A concise (nine-step) and effective (19% overall yield) total synthesis of ningalin D (1a) is disclosed and is based on a key 1,2,4,5-tetrazine --> 1,2-diazine --> pyrrole Diels-Alder strategy to assemble a fully substituted pyrrole core central to its structure. Additional highlights of the synthesis include a double Dieckmann condensation to introduce the C and D aryl rings enlisting substituents judiciously placed on the dienophile and intrinsic to the widely used tetrazine 2, a highly effective Suzuki coupling of the resulting C and D phenol triflates for introduction of the sterically demanding F and G aryl rings, and an unusually effective formal oxidative decarboxylation reaction cascade initiated by a Curtius rearrangement to directly provide the biphenylene quinone methide found imbedded in the structure of ningalin D. The cytotoxic and multidrug resistance (MDR) reversal activity of ningalin D, its derivatives, and the key synthetic intermediates are detailed.
90 citations
TL;DR: In this article, the Claisen-Schmidt condensation of benzaldehyde with 2-butanone was investigated and is used to demonstrate the ability to conduct conventionally acid or base catalyzed reactions homogeneously using NCW without the addition of a catalyst.
88 citations
TL;DR: In this article, the Dieckmann condensation of this diester using potassium hydride afforded 2-ethoxycarbonylcyclo-9-heptadecenone, which was converted by hydrolysis and decarboxylation to cyclo 9-hexadecene (civetone) as a mixture of cis and trans isomers in 54% yield.
85 citations
TL;DR: In this article, the dieckmann condensation reactions of diethyl adipate and pimelate were conducted in the absence of solvent, and the reaction products were collected by a direct distillation from the solvent-free reaction mixture.
Abstract: Dieckmann condensation reactions of diethyl adipate and pimelate proceeded efficiently in the absence of solvent, and the reaction products were collected by a direct distillation from the solvent-free reaction mixture.
64 citations
TL;DR: The first total synthesis of (-)-fusarisetin A, the enantiomer of naturally occurring acinar morphogenesis inhibitors, was accomplished in 13 steps, leading to the reassignment of the absolute configuration of the natural product.
Abstract: The first total synthesis of (−)-fusarisetin A, the enantiomer of naturally occurring acinar morphogenesis inhibitor (+)-fusarisetin A, was accomplished in 13 steps, leading to the reassignment of the absolute configuration of the natural product. The synthesis featured a Lewis acid-promoted intramolecular Diels–Alder reaction, a Pd-catalyzed O→C allylic rearrangement, a chemoselective Wacker oxidation, and a Dieckmann condensation/hemiketalization cascade.
62 citations