Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol  

作　　者：Pablo A.Chacón-Morales Juan M.Amaro-Luis Luis Beltrán Rojas Fermín Rémi Jacquet Denis Deffieux Laurent Pouységu Stéphane Quideau 

机构地区：[1]Natural Products Laboratory,Department of Chemistry,Faculty of Science,University of Los Andes,Mérida 5101,Venezuela [2]Research Institute,Faculty of Pharmacy and Bioanalysis,University of Los Andes,Mérida 5101,Venezuela [3]ISM(CNRS-UMR 5255),Univ.Bordeaux,351 cours de la Libération,33405 Talence Cedex,France

出　　处：《Natural Products and Bioprospecting》2022年第1期265-269,共5页应用天然产物（英文）

基　　金：supported by the National Fund of Science,Technology and Innovation (FONACIT) (Grant N°201300288)within the framework of the project PCP France-Venezuela;by the CDCHTA-ULA (Grant N°C-1935-15-08-ED).

摘　　要：From aerial parts of Austroeupatorium inulifolium was isolated the ent-nor-furano triol labdane austroeupatol 1.The compound 1 was treated with IBX showing an unexpected selectivity at the potentially oxidizable sites of the sub-strate yielding the 2-oxoaustroeupatol(2)and 2,19-dioxoaustroeupatol(3).The treatment of 2 with sodium periodate yields a heterocyclic derivative(ε-caprolactone derivate 4)formed by oxidative cleavage and unexpected intramo-lecular attack of the hydroxymethylene(C-19)oxygen to the ketonic carbon(C-2).A plausible mechanistic pathway for the obtention of compound 4 is proposed.

关 键 词：Oxidative cleavage Austroeupatol NaIO4 IBX LACTONIZATION NMR 

分 类 号：O62[理学—有机化学]