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

被引：7
|
作者：
Lewis, Wilfred J. M. [1 ]
Shaw, David M. [2 ,3 ]
Robertson, Jeremy [1 ]
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England
[2] Vertex Pharmaceut Europe Ltd, 86-88 Jubilee Ave,Milton Pk, Abingdon OX14 4RW, Oxon, England
[3] Francis Crick Inst, MSD UK Discovery Ctr, 1 Midland Rd, London NW1 1AT, England
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 17卷
基金：
英国工程与自然科学研究理事会;
关键词：
acyloxypyrroles; bacterial pyrrolizidines; cyanoketones; legonmycin; vinylogous ureas; STREPTOMYCES SP; CLAZAMYCIN-A; JENAMIDINE-A; DERIVATIVES; BOHEMAMINE; BIOSYNTHESIS; DISCOVERY; ALKALOIDS;
D O I：
10.3762/bjoc.17.31
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-l-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.
引用
收藏
页码：334 / 342
页数：9
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