New synthesis and application of 3-substituted prolinols

被引：17
|
作者：
Chang, MY [1 ]
Chen, CY
Tasi, MR
Tseng, TW
Chang, NC
机构：
[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan
[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
来源：
SYNTHESIS-STUTTGART | 2004年 / 06期
关键词：
glutarimides; stepwise [3+2] annulation; pyroglutamates; prolinol; isoguvacine; paroxetine;
D O I：
10.1055/s-2004-816001
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Carbon skeleton of polysubstituted pyroglutarnates with three contiguous asymmetric centers was built up in one base-induced coupling/cyclization reaction of alpha-sulfonylacetamide with 2-bromo-2-propenoates. A simple transformation to 3-substituted prolinols can be easily achieved via reduction and desulfonation. A ring expansion of prolinol has been used as the key step in the formal synthesis of isoguvacine and paroxetine. The one-pot conversion of 3-substituted prolinol to the 3-Substituted pyroglutamic acid is also reported.
引用
收藏
页码：840 / 846
页数：7
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