54705-70-3Relevant academic research and scientific papers
Use of the potassium ion as a template for the selective derivatization of the antibiotic X-206
O'Sullivan, Anthony C.,Struber, Fritz,Ley, Steven V.
, p. 6252 - 6256 (1999)
The templating effect of potassium ions on the ionophore antibiotic X- 206 (1) ensured that most of the hydroxy, hemiacetal, and ether groups were involved in encapsulation of the metal atom, which allowed a selective derivatization at the unbound C(22) p
Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles
Barbasiewicz, Micha?,Tryniszewski, Micha?
, (2021/11/30)
A series of acyl fluorides was synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at room temperature, followed by extraction and distillation. Isolated acyl fluorides (usually 7-20 g) display excellent purity and can be transformed into sterically hindered amides and esters when treated with lithium amide bases and alkoxides under mild conditions.
1,2-asymmetric induction in diastereoselective zwitterionic aza-Claisen rearrangements: Key steps in optically active alkaloid synthesis
Heescher, Carolin,Schollmeyer, Dieter,Nubbemeyer, Udo
supporting information, p. 4399 - 4404 (2013/07/26)
The zwitterionic aza-Claisen rearrangement of optically active N-allylpyrrolidines and α-phenoxyacetyl fluorides proceeds with complete simple diastereoselectivity (internal asymmetric induction) and complete 1,2-asymmetric induction to generate a new C-C bond adjacent to a chiral C-N-Boc functionality. The resulting γ,δ-unsaturated amides were cyclised to give the corresponding pyrrolizidinones, which enabled the determination of the relative configuration of the stereotriads. Vinyl group degradation and a final lactam reduction gave an optically active analogue of (+)-petasinine (a pyrrolizidine alkaloid). Furthermore, the stereotriad-containing amides should be useful key intermediates for the total synthesis of optically active elaeocarpin (an indolizidine alkaloid). Copyright
