Enantioselective total syntheses and determination of absolute configuration of marine toxins, oxazinins

被引：5
|
作者：
Dethe, Dattatraya H. [1 ]
Ranjan, Alok [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
RSC ADVANCES | 2013年 / 3卷 / 45期
关键词：
STEREOCHEMISTRY; MUSSELS; DEPROTECTION; BURSATELLIN; ASSIGNMENT;
D O I：
10.1039/c3ra44631j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The enantioselective total syntheses of natural marine toxins, oxazinin-1, -2, -4, -5, -6 and linear precursor preoxazinin-7 are described. The synthetic highlights include Sharpless asymmetric aminohydroxylation and dihydroxylation, oxa-Michael reaction and intramolecular diastereoselective addition of an appropriate hydroxyl substituent to a 3-methyleneindolenine for the construction of the morpholine ring as key steps. The synthetic route also allowed the synthesis of the epi-preoxazinin and a structurally related secondary metabolite bursatellin isolated in 1980 from sea hare Bursatella leachii pleii and its epimer.
引用
收藏
页码：23692 / 23703
页数：12
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