天然产物的绝对构型研究(Ⅰ)——通过比较旋光和碳谱的实验值与计算值确定酮类、内酯类和醇类化合物的绝对构型

摘要

Optical rotation and 13C NMR computations for five natural products, vidalenolone(1) , 2-(3-di hydroxy-3-methylbutyl)benzene-1,4-diol(2), 5,6,7,7a(S)-tetrahydro-2-hydroxy-l-( p-hydroxyphenyl)-3H-pyrolizin-3-one(3) , 3 ,4-dihydro-4,8-dihydroxy-6-methoxy-7-methyl-l (2H)-naphthalenone(4) and 6-(R)-(4'-oxopentyl)-5,6-dihydro-2H-pyran-2-one(5), were performed at the B3LYP/aug-cc-pVDZ//B3LYP/6- 31G(d) levels for assigning their absolute configurations. The computational results matched the experimental results well. One compound's 13C NMR chemical shifts were corrected based on the computational 13C NMR results and earliest reports.%在研究天然产物绝对构型的过程中,筛选了系列绝对构型未鉴定的化合物,在B3 LYP/aug-cc-pVDZ//B3 LYP/6-31G(d)水平上计算了它们的旋光和碳谱数据.结果表明,计算结果与实验数值十分符合,从而鉴定出了这些化合物的绝对构型.另外,根据计算结果和早期实验报告更正了1个化合物的碳谱化学位移.