The first preparation of enantiopure 1-methyl-7-oxabicyclo[2.2.1]heptan-2-one, a versatile chiral building block for terpenoids

被引：6
|
作者：
Guan, YK
Li, YL [1 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Inst Organ Chem, Lanzhou 730000, Peoples R China
来源：
CHIRALITY | 2005年 / 17卷 / 02期
关键词：
absolute configuration; chemical resolution; kinetic resolution; mandelic acid; sesquiterpenoids;
D O I：
10.1002/chir.20095
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Methods for the resolution of (+/-)-l-methyl-7-oxabicyclo[2.2.1]heptan-2-one 1, a versatile chiral building block for terpenoids, have been investigated. While no efficient result was obtained with kinetic resolution methods, both enantiomers of 1 were prepared optically pure for the first time via esterification of the reductive products of 1 with (+)-mandelic acid and oxidation of the saponified products of diastereomer esters, in an overall yield of 70%. The absolute configurations of (-)-l and (+)-l were determined as (IS,4R)-(-)-1 and (1R,4S)-(+)-1 by the CD exciton chirality method and confirmed by Moshers H-1-NMR method. Chirality 17:113-118, 2005. (C) 2005 Wiley-Liss, Inc.
引用
收藏
页码：113 / 118
页数：6
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