Total synthesis of 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide and 3,7-dimethyl-2,6-octadien-1,6-olide
Authors:
- 25 June 2013
- journal article
- research article
- Published by Taylor & Francis in Journal of Asian Natural Products Research
- Vol. 15 (8) , 880-884
Abstract
3,7-Dimethyl-7-hydroxy-2-octen-1,6-olide (1) and 3,7-dimethyl-2,6-octadien-1,6-olide (2), the natural bioactive compounds isolated from the fruit of Litsea cubeba and the liverwort Plagiochila rutilans, were totally synthesized using easily available cis-geraniol as raw material in short, convenient, and low-cost, five-step reactions including three steps of oxidation, cyclization, and dehydration, with an overall yield of 47.5% and 37.3%.Keywords
This publication has 23 references indexed in Scilit:
- Claurailas A−D, Cytotoxic Carbazole Alkaloids from the Roots of Clausena harmandianaJournal of Natural Products, 2011
- The Fungicidal Terpenoids and Essential Oil from Litsea cubeba in TibetMolecules, 2010
- Highly efficient synthesis of medium-sized lactones via oxidative lactonization: concise total synthesis of isolaurepanOrganic & Biomolecular Chemistry, 2009
- Substrate Encapsulation: An Efficient Strategy for the RCM Synthesis of Unsaturated ϵ-LactonesOrganic Letters, 2008
- Neric acid derivatives produced by the honey bee fungal entomopathogen Ascosphaera apisPhytochemistry Letters, 2008
- Natural occurrence, biological activities and synthesis of eight-, nine-, and eleven-membered ring lactonesQuímica Nova, 2008
- Synthesis of epoxy dinitriles from citral and their acid-catalyzed transformationsRussian Journal of Organic Chemistry, 2007
- Anti-inflammatory and Analgesic Effects of Drypemolundein A, a Sesquiterpene Lactone from Drypetes molunduanaPharmaceutical Biology, 2003
- Coumarins and Carbazoles with Antiplasmodial Activity from Clausena harmandianaPlanta Medica, 2000
- Structure-odor relationships in monoterpenelactones.Agricultural and Biological Chemistry, 1990