Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines
Wilfred J. M. Lewis, David M. Shaw, Jeremy Robertson
Abstract
A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1 H -pyrrolizin-1-one affords the Streptomyces secondary metabolites legonmycins A and B – three operations overall from methyl N -Boc-prolinate. The key step proceeds in each case via N , O -diacylation, then selective oxidative hydrolysis of the intermediate bicyclic pyrrole and establishes a precedent for the synthesis of related C(7a)-hydroxylated pyrrolizidines.
Topics & Concepts
ChemistryPyrroleBicyclic moleculeHydrolysisStereochemistryCombinatorial chemistryOrganic chemistryPlant Toxicity and Pharmacological PropertiesMicrobial Natural Products and BiosynthesisPlant and fungal interactions