5096-50-4Relevant academic research and scientific papers
Tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes. 11. The synthesis of (+)-crotanecine
Denmark, Scott E.,Thorarensen, Atli
, p. 125 - 137 (2007/10/03)
(+)-Crotanecine (1) is the necine base component of a number of pyrrolizidine alkaloids. This necine subunit is an amino triol bearing a primary allylic alcohol characterized by an all-cis relationship of its stereocenters. The synthesis of (+)-crotanecine has been accomplished in 10 steps and 10.2% overall yield. The key step in the asymmetric synthesis is a Lewis acid-promoted, tandem inter[4 + 2]/intra[3 + 2] cycloaddition between a (fumaroyloxy)nitroalkene 14 and chiral β-silylvinyl ether (-)-26. This synthesis serves to illustrate the synthetic versatility of the tandem cycloaddition to incorporate additional functionality.
An enantioselective synthesis of (+)-crotanecine by an intramolecular azide 1,3-dipolar cycloaddition
Bennett III,Cha
, p. 5437 - 5440 (2007/10/02)
An efficient, enantioselective synthesis of (+)-crotanecine (1) has been accomplished by an intramolecular azide [2+3] dipolar cycloaddition starting from 2,3-O-isopropylidene-D-erythrose (8).
AN ENANTIOSELECTIVE SYNTHESIS OF (+)-CROTANECINE
Yadav, Veejendra Kumar,Rueeger, Heinrich,Benn, Michael
, p. 2735 - 2738 (2007/10/02)
(2S,4R)-4-Hydroxyproline was elaborated into (+)-crotanecine via (1S,5R,8R)-8-hydroxy-2-oxa-6-azabicyclooctan-3-one
