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.
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页数：8
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