Preparation of Enantiomerically Pure 1-Methyl-7-oxabicyclo[2.2.1]heptan-2-one

Abstract

Abstract: (±)-1-Methyl-7-oxabicyclo[2.2.1]heptan-2-one (1) is a versatile chiral building block for terpenoids. It could be applied in total synthesis of eudesmanes, agarofurans and norcarotenoids. Compound (±)-1 was reduced to alcohol (±)-2. Compound (±)-2 was esterified with commercial available optically pure (S)-(+)-mandelic acid. The diastereomeric ester mixture was separated with preparative HPLC method. After oxidation of the saponified products of diastereomeric ester (+)-4 and (+)-5 respectively, both optically pure enantiomers of compound 1 were prepared for the first time in four steps with an overall yield of 70%. The absolute configurations of (+)-1 and (-)-1 were determined as (+)-(1R,4S)-1-methyl-7-oxabicyclo[2.2.1] heptan-2-one and (-)-(1S,4R)-1-methyl-7-oxabicyclo[2.2.1] heptan-2-one.

Key words: 1-Methyl-7-oxabicyclo[2.2.1]heptan-2-one, Terpenoids, Mandelic acid, Resolution

CLC Number:

O621

TrendMD:

GUAN Yu-Kun, FANG Li-Jing, ZHENG Guo-Jun, LI Yu-Lin. Preparation of Enantiomerically Pure 1-Methyl-7-oxabicyclo[2.2.1]heptan-2-one[J]. Chem. J. Chinese Universities, 2005, 26(2): 264.

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Preparation of Enantiomerically Pure 1-Methyl-7-oxabicyclo[2.2.1]heptan-2-one

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