61188-00-9Relevant articles and documents
Total Synthesis of (+)-Antrocin and Its Diastereomer and Clarification of the Absolute Stereochemistry of (-)-Antrocin
Huang, Sheng-Han,Liang, Kai-Hsiang,Lu, Jia-Syun,Chang, Wei-Sheng,Su, Ming-Der,Yang, Te-Fang
, p. 9576 - 9584 (2017)
Using 2,2-dimethyl cyclohexanone as the starting compound, (+)-antrocin and its diastereomer have been synthesized. The absolute stereochemistry of (-)-antrocin, a natural sesqui-terpenoid and an antagonist in some types of cancer cells, was clarified using the character data of (+)-antrocin. The synthetic procedure involved two key steps: (1) the reaction of vinyl magnesium bromide with 2,2-dimethyl-6-t-butyl-dimethyl-silyoxy-methyl-1-cyclo-hexanone to give a vinyl cyclohexanol derivative and (2) a highly stereoselective intramolecular Diels-Alder (IMDA) reaction of the camphanate-containing triene intermediate. The relative energy levels of the possible transition states of the IMDA reaction of the camphanate-containing triene were obtained from density functional theory calculations, proving the stereospecific formation of the target molecule.
First total synthesis and assignment of the stereochemistry of crispatenine
Bourdron, Julien,Commeiras, Laurent,Audran, Gerard,Vanthuyne, Nicolas,Hubaud,Parrain, Jean-Luc
, p. 3770 - 3775 (2008/02/04)
(Figure Presented) The first racemic and enantioselective synthesis of crispatenine 1 has been achieved, which involved a few steps, enabling the assignment of the absolute and relative configurations.