A short, efficient, and stereoselective total synthesis of a pyrrolidine alkaloid: (-)-codonopsinine.
An efficient total synthesis of antibiotic (-)-codonopsinine 1 with an overall yield of 44% was achieved from d-alanine as a chiral template. The key steps in our strategy are modified Sharpless asymmetric dihydroxylation reaction and the highly stereoselective intramolecular acid-catalyzed amidocyclization.
Reddy
Jangari Santhosh
JS
Organic Division III, Indian Institute of Chemical Technology, Hyderabad 500007, India.
Rao
Batchu Venkateswara
BV
D000470:Alkaloids / Q000138:chemical synthesis*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D011759:Pyrrolidines; C415669:codonopsinine; C032519:pyrrolidine