Next Article in Journal
Two New Secondary Metabolites from Xylaria sp. cfcc 87468
Previous Article in Journal
Synthesis of Tetrahydrohonokiol Derivates and Their Evaluation for Cytotoxic Activity against CCRF-CEM Leukemia, U251 Glioblastoma and HCT-116 Colon Cancer Cells
Article Menu

Export Article

Open AccessArticle
Molecules 2014, 19(1), 1238-1249; doi:10.3390/molecules19011238

Construction of the 1,2-Dialkenylcyclohexane Framework via Ireland-Claisen Rearrangement and Intramolecular Barbier Reaction: Application to the Synthesis of (±)-Geijerone and a Diastereoisomeric Mixture with Its 5-Epimer

Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, Liaoning, China
*
Author to whom correspondence should be addressed.
Received: 17 December 2013 / Revised: 14 January 2014 / Accepted: 15 January 2014 / Published: 20 January 2014
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [255 KB, uploaded 18 June 2014]   |  

Abstract

The elemene-type terpenoids, which possess various biological activities, contain a syn- or anti-1,2-dialkenylcyclohexane framework. An efficient synthetic route to the syn- and anti-1,2-dialkenylcyclohexane core and its application in the synthesis of (±)-geijerone and its diastereomer is reported. Construction of the syn- and anti-1,2-dialkenyl moiety was achieved via Ireland-Claisen rearrangement of the (E)-allylic ester, and the cyclohexanone moiety was derived from the iodoaldehyde via intramolecular Barbier reaction. The synthetic strategy allows rapid access to various epimers and analogues of elemene-type products.
Keywords: 1,2-dialkenylcyclohexane; (±)-geijerone; Ireland-Claisen rearrangement; intramolecular barbier reaction; synthesis 1,2-dialkenylcyclohexane; (±)-geijerone; Ireland-Claisen rearrangement; intramolecular barbier reaction; synthesis
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Liang, D.; Gao, N.; Liu, W.; Dong, J. Construction of the 1,2-Dialkenylcyclohexane Framework via Ireland-Claisen Rearrangement and Intramolecular Barbier Reaction: Application to the Synthesis of (±)-Geijerone and a Diastereoisomeric Mixture with Its 5-Epimer. Molecules 2014, 19, 1238-1249.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top