A reactive lactonic dienophile – 3-carbethoxy-5,5-dimethyl-2(5H)-furanone. Application to the synthesis of a monoterpenoid lactone
- 1 April 1982
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 60 (7) , 921-925
- https://doi.org/10.1139/v82-138
Abstract
In contrast to the low dienophilicity generally observed for .alpha.,.beta.-unsaturated lactones, the title compound 2 is a reactive dienophile. Under stannic chloride catalysis, it undergoes Diels-Alder reaction regio- and stereoselectively with a variety of dienes at room temperature. The synthesis of (.+-.)-o-mentha-1,3-dien-1 .fwdarw. 8-olide (20) [found in Phascolarctos cinereus urine] was achieved by a 2-step sequence using lactone ester 2. Addition of 2 to 1-acetoxy-1,3-butadiene afforded epimeric acetoxy lactones which were converted to the monoterpenoid lactone 20 by treatment with lithium iodide dihydrate in collidine.This publication has 1 reference indexed in Scilit:
- Total synthesis of α- and β-himachalene by an intermolecular Diels–Alder approachCanadian Journal of Chemistry, 1981