Desymmetrization of 3-dimethyl(phenyl)silyl glutaric anhydride with Evans’ oxazolidinone: an application to stereocontrolled synthesis of the antifungal agent (+)-preussin
Desymmetrization of 3-dimethyl(phenyl)silyl glutaric anhydride with Evans’ oxazolidinone: an application to stereocontrolled synthesis of the antifungal agent (+)-preussin
复制标题
Evans 恶唑烷酮对 3-二甲基（苯基）甲硅烷基戊二酸酐的去对称化：在抗真菌剂 (+)-普鲁士素立体控制合成中的应用
DOI：
--
复制
发表时间：
1999
期刊：
影响因子：
--
通讯作者：
S. Ghosh
中科院分区：
文献类型：
--
作者：
R. Verma;S. Ghosh
A stereoselective total synthesis of (+)-preussin (1) has been achieved from the σ-symmetric 3-dimethyl(phenyl)silyl substituted glutaric anhydride 4 featuring its desymmetrization using Evans’ oxazolidinone 10. The first homochiral intermediate, the glutarate half-ester 9 was obtained from both the diastereoisomeric acids 11a and 12a in a convergent fashion. The dimethyl(phenyl)silyl group is not only acting as a masked hydroxy group but also restricts elimination reactions and facilitates Curtius reaction. It also stereodirects ester enolate alkylation of 18 and hydrogenation of intermediate Δ1-pyrroline 5.
