81987-51-1Relevant 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).
CLAISEN-REARRANGEMENT-MEDIATED RING CONTRACTION OF MACROCYCLIC LACTONES A NEW APPROACH TO CARBOCYCLES AND HETEROCYCLES
Funk, Raymond L.,Abelman, Matthew, M.,Munger, John D.
, p. 2831 - 2846 (2007/10/02)
Macrocyclic ketene acetals 3 undergo Claisen rearrangements smoothly and constitute a viable and general approach to hetero- or carbocyclic ring systems 4.This novel ring contraction process is subject to high internal asymmetric induction (cf. lactones 7 -> carbocycles 8) as well as relative asymmetric induction in the rearrangements of ketene acetals derived from lactones 18, 23 and 27.Finally, N-benzoylmeroquinene methyl ester (37) was prepared to demonstrate the potential of this methodology in heterocycle synthesis.
