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Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines. | LitMetric

Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines.

Beilstein J Org Chem

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom.

Published: February 2021

A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1-pyrrolizin-1-one affords the secondary metabolites legonmycins A and B - three operations overall from methyl -Boc-prolinate. The key step proceeds in each case via ,-diacylation, then selective oxidative hydrolysis of the intermediate bicyclic pyrrole and establishes a precedent for the synthesis of related C(7a)-hydroxylated pyrrolizidines.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7871033PMC
http://dx.doi.org/10.3762/bjoc.17.31DOI Listing

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