Olefin metathesis based approach to diversely functionalized pyrrolizidines and indolizidines; total synthesis of (+)-monomorine.
New scaffolds for the stereoselective synthesis of diversely functionalized chiral enantiopure indolizidines and pyrrolizidines 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.
Lesma
Giordano
G
Dipartimento di Chimica Organica e Industriale, Universita degli Studi di Milano, via G. Venezian 21, 20133 Milano, Italy. giordano.lesma@unimi.it
Colombo
Alessia
A
Sacchetti
Alessandro
A
Silvani
Alessandra
A
D000475:Alkenes / Q000737:chemistry*; D054836:Indolizidines / Q000138:chemical synthesis*; D007212:Indolizines / Q000138:chemical synthesis*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000475:Alkenes; D054836:Indolizidines; D007212:Indolizines; D011763:Pyrrolizidine Alkaloids; C538734:monomorine