(±)-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 ...(±)-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.展开更多
Aim Syntheses of benzodioxane neolignans. Method The SN2 reaction and Corey-Fuchs reaction was used to synthesize Rodgersinine A, 4-[3-methyl-7-[（E）-1-propenyl-2, 3-dihydro-1, 4-benzodioxin-2-yl]-l, 2-benzenediol （...Aim Syntheses of benzodioxane neolignans. Method The SN2 reaction and Corey-Fuchs reaction was used to synthesize Rodgersinine A, 4-[3-methyl-7-[（E）-1-propenyl-2, 3-dihydro-1, 4-benzodioxin-2-yl]-l, 2-benzenediol （1） and Rodgersinine B, 4- [3-methyl- 7-（1-propynyl）-2, 3-dihydro- 1, 4-benzodioxin-2-yl]-0, 2-benzenediol （2）. Results Total synthesis ofRodgersinine A and B was first completed. Conclusion A useful method for constructing benzodioxane neolignans by the SN2 reaction is achieved.展开更多
文摘(±)-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.
基金Program for Changjiang Scholars and Innovative Team in University(985-2-063-112).
文摘Aim Syntheses of benzodioxane neolignans. Method The SN2 reaction and Corey-Fuchs reaction was used to synthesize Rodgersinine A, 4-[3-methyl-7-[（E）-1-propenyl-2, 3-dihydro-1, 4-benzodioxin-2-yl]-l, 2-benzenediol （1） and Rodgersinine B, 4- [3-methyl- 7-（1-propynyl）-2, 3-dihydro- 1, 4-benzodioxin-2-yl]-0, 2-benzenediol （2）. Results Total synthesis ofRodgersinine A and B was first completed. Conclusion A useful method for constructing benzodioxane neolignans by the SN2 reaction is achieved.
