A glycal based approach to the synthesis of (+)-bulgecinine, 3-hydroxy-2,5-dihydroxymethylpyrrolidine and 2-oxapyrrolizidin-3-one

被引：2

作者：

Mishra, Umesh K. ^{[1
]}

Ramesh, Namakkal G. ^{[1
]}

机构：

[1] Indian Inst Technol Delhi, Dept Chem, New Delhi 110016, India

来源：

CARBOHYDRATE RESEARCH | 2020年 / 489卷

关键词：

Bulgecinine; Glycal; Glycosidase inhibitors; Natural product; Pyrrolizidine; EFFICIENT STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREODIVERGENT SYNTHESIS; BACTERIAL METABOLITES; ASYMMETRIC-SYNTHESIS; RADICAL CYCLIZATION; BULGECIN; ROUTE; (-)-BULGECININE; DERIVATIVES;

D O I：

10.1016/j.carres.2020.107931

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A glycal based synthesis of ( + )-bulgecinine, 3-hydroxy-2,5-dihydroxymethylpyrrolidine and 2-oxapyrrolizidin-3-ones proceeding through a common intermediate is reported. The key step in the work presented here is a two-step conversion of 4,6 di-O-benzyl-D-glucal to 2,3-dideoxy-2-tosylamido-D-glucose. This manuscript reports the first carbohydrate based approach to the synthesis of ( + )-bulgecinine and the whole sequence has been accomplished with complete stereochemical integrity without the formation of mixture of products in any of these steps.

引用

页数：8

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