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

页码：840 / 846

页数：7

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