863660-29-1Relevant academic research and scientific papers
Olefin metathesis based approach to diversely functionalized pyrrolizidines and indolizidines; total synthesis of (+)-monomorine
Lesma, Giordano,Colombo, Alessia,Sacchetti, Alessandro,Silvani, Alessandra
experimental part, p. 590 - 596 (2009/06/20)
New scaffolds for the stereoselective synthesis of diversely functionalized chiral enantiopure indolizidines and pyrrolidines were synthesized from the cross and ring-closing metathesis reactions of appropriate intermediates, readily available from L-pyroglutamic acid. The versatility of this strategy was demonstrated by the synthesis of an indolizidine-based azasugar analogue and of the natural alkaloid (+)-monomorine.
A new spirocyclic proline-based lactam as efficient type II′ β-turn inducing peptidomimetic
Lesma, Giordano,Colombo, Alessia,Sacchetti, Alessandro,Silvani, Alessandra
body text, p. 7423 - 7425 (2009/05/11)
A new proline-based spirotricyclic lactam is reported as an efficient type II′ β-turn inducing peptidomimetic. After investigations of the reverse turn properties by computational techniques, the scaffold has been synthesized by a straightforward sequence relying on a key RCM reaction for the construction of the spirocyclic lactams ring. For its conformational properties, the scaffold can be considered a privileged structure to be employed as a mimic of the β-turn motif of the potent antibiotic Gramicidin S.
A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis
Aggarwal, Varinder K.,Astle, Christopher J.,Rogers-Evans, Mark
, p. 1469 - 1471 (2007/10/03)
Enyne metathesis has been used to prepare bridged azabicycles and applied in a short asymmetric synthesis of the tropane ferruginine. A Grubbs first generation catalyst proved to be superior to the second generation catalyst in the enyne metathesis reaction.
