莱戈霉素A、B（C(7a)-羟基化细菌吡咯里西啶）的合成。

Lewis Wilfred J M, Shaw David M, Robertson Jeremy

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

Vertex Pharmaceuticals (Europe) Ltd., 86-88 Jubilee Avenue, Milton Park, Abingdon, OX14 4RW, United Kingdom.

Beilstein J Org Chem. 2021 Feb 2;17:334-342. doi: 10.3762/bjoc.17.31. eCollection 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.

一种从3-氨基-2-甲基-5,6,7,7a-四氢-1-吡咯里嗪-1-酮出发的单瓶两步法可得到次级代谢产物莱戈霉素A和B——从Boc-脯氨酸甲酯开始总共需要三步操作。关键步骤在每种情况下均通过γ,δ-二酰化进行，然后对中间体双环吡咯进行选择性氧化水解，为相关C(7a)-羟基化吡咯里西啶的合成建立了先例。