NEW ASYMMETRIC-SYNTHESIS OF (-)-ESERMETHOLE

被引：37

作者：

PALLAVICINI, M ^{[1
]}

VALOTI, E ^{[1
]}

VILLA, L ^{[1
]}

RESTA, I ^{[1
]}

机构：

[1] BIOCHIM OPOS SPA,I-20041 AGRATE BRIANZA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(00)86207-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new synthesis of (-)-esermethole, based on the asymmetric alkylation at C(3) of racemic 1,3-dimethyl-5-methoxyoxindole (3), is described. The chloroacetyl derivatives of (-)-menthol and (S)-N-methyl-(1-phenylethyl) amine were chosen as chiral alkylating agents and used under different reaction conditions (temperature, solvent and base). In particular, the latter reacted with 3 in toluene at 10-degrees-C, in the presence of t-butyllitium, giving (3S,1'S)-N-methyl-N-(1'-phenylethyl)-1,3-dimethyl-5-methoxyoxindol-3-ilacetamide (10) with a 63% d.e.. This intermediate was easily separated from the undesired minor (3R,1'S) diastereomer (11) and converted to (-)-esermethole (99.6% e.e.) in two steps.

引用

页码：363 / 370

页数：8