98216-93-4Relevant articles and documents
A palladium-catalyzed aminoalkynylation strategy towards bicyclic heterocycles: Synthesis of (±)-trachelanthamidine
Nicolai, Stefano,Piemontesi, Cyril,Waser, Jerome
supporting information; experimental part, p. 4680 - 4683 (2011/06/23)
Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium-catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS-EBX. After removal of the protecting group, a two-step cyclization sequence and subsequent reduction led to the natural product (±)-trachelanthamidine (see scheme; TIPS-EBX=triisopropylsilyl ethynylbenziodoxolone).
Reaction of Novel Imide Reducing Reagents with Pyrrolizidinediones
Thomas, Edward W.,Rynbrandt, Ronald H.,Zimmermann, David C.,Bell, Larry T.,Muchmore, Christine R.,Yankee, Ernest W.
, p. 4535 - 4543 (2007/10/02)
The reduction of pyrrolizidinediones 4a and 4b with (i-Bu)2AlH and LiBHEt3 affords the corresponding hexahydro-5-hydroxy-3H-pyrrolizin-3-ones 8a and 8b in good yield.LiBHEt3 also reduces N-methylglutarimide (18) in 53percent yield.The combination of NaBH4/MeOH/Ac2O/CH2Cl2 selectivity reduces an imide in the presence of an ester.Hexahydro-5-(methylthio)-3H-pyrrolizin-3-ones are products of the NaBH4 reduction of pyrrolizidinediones in MeSH/CH2Cl2/Ac2O.The reduction products, thioethers (5a-c) and lactamols (8a-c), are intermediates in the synthesis of pyrrolizinones 1a-c.
