SYNTHESIS AND DETERMINATION OF THE RELATIVE STEREOCHEMISTRY OF A NEW EPOXIDE ALDEHYDE CYCLOPENTANE MONOTERPENOID

Química Nova

Cunha Neto, Álvaro¹  Faria, Bruna B. de¹  Felippe, Igor Simões A.¹  Universidade Federal do Espirito Santo, Vitória, Brasil¹  Lacerda Jr., Valdemar¹  Leite, Júlia de Almeida¹  M. Junior, Elizeu de Souza¹  Santos, Reginaldo B. dos¹  Greco, Sandro J.¹ 

关键词:  plinol;    limonene oxide;    cyclopentane;    monoterpenoid;   

DOI  :  10.5935/0100-4042.20150151

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 摘 要 】

In this study, we report the preparation of a new tetra-substituted epoxide aldehyde cyclopentane, which acts as a starting material for the synthesis of plinol, from (R)-(+)-epoxy-limonene. The synthesis was performed in three steps and resulted in a good yield. The structural determination was performed by 1H and 13C NMR, and the relative stereochemistry was defined by nuclear Overhauser effect (NOE) experiments with computer calculations of molecular modeling, particularly with respect to indirect coupling constant calculations.

【 授权许可】

Unknown