Convenient approach to an advanced intermediate for salinosporamide A synthesis

被引：1
|
作者：
Takacsova, Margareta [1 ]
Conlcova, Miroslava [1 ]
Martinkova, Miroslava [1 ]
Gonda, Jozef [1 ]
机构：
[1] Safarik Univ, Inst Chem Sci, Dept Organ Chem, Moyzesova 11, SK-04001 Kosice, Slovakia
来源：
TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 7-8期
关键词：
PROTEASOME INHIBITOR NPI-0052; CONCISE TOTAL-SYNTHESIS; ALPHA-AMINO-ACID; FORMAL SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CANCER-THERAPY; REARRANGEMENT; BORTEZOMIB; APOPTOSIS;
D O I：
10.1016/j.tetasy.2016.03.003
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An approach towards the advanced scaffold 21 as an intermediate for salinosporamide A 1 synthesis has been developed starting from the known ulose 3. This strategy involves the 2-hydroxyethyl moiety installation at the C-5 position via a Wittig transformation followed by Pd/C-mediated hydrogenation of the conformationally constrained alkene 9 in a stereoselective manner, and the Overman rearrangement, thus allowing full control over the configuration of the newly generated quaternary stereocentre with an amino group in 18. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：369 / 376
页数：8
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