Next Article in Journal
Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity
Previous Article in Journal
Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana
Previous Article in Special Issue
Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins
Molecules 2014, 19(2), 1748-1762; doi:10.3390/molecules19021748
Article

Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds

1,2, 1,3, 2,*  and 1,*
1 Department of Organic Chemistry and Institute of Biotechnology, University of Granada, Avda Fuentenueva s/n, 18071 Granada, Spain 2 CIQSO–Center for Research in Sustainable Chemistry and Department of Chemical Engineering, Physical Chemistry and Organic Chemistry, University of Huelva, Avda 3 Marzo s/n, 21071 Huelva, Spain 3 University of Antioquia, Calle 70 N° 52-21, Medellín, Colombia
* Authors to whom correspondence should be addressed.
Received: 19 December 2013 / Revised: 22 January 2014 / Accepted: 23 January 2014 / Published: 3 February 2014
(This article belongs to the Special Issue Domino Reactions)
View Full-Text   |   Download PDF [420 KB, 18 June 2014; original version 18 June 2014]   |   Browse Figures

Abstract

The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a D1,6-double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive trisporoid family. The synthetic sequence consists of the preparation of a properly functionalized epoxygeraniol derivative, and its subsequent stereoselective cyclization mediated by Ti(III). This last step implies a domino process that starts with a homolytic epoxide opening followed by a radical cyclization and regioselective elimination. This concerted process gives access to the cyclohexane moiety with stereochemical control of five of its six carbon atoms.
Keywords: trisporoids; apocarotenoid; domino reaction; stereoselective synthesis trisporoids; apocarotenoid; domino reaction; stereoselective synthesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

González-Delgado, J.A.; Escobar, G.; Arteaga, J.F.; Barrero, A.F. Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds. Molecules 2014, 19, 1748-1762.

View more citation formats

Supplement

Related Articles

Article Metrics

Comments

Citing Articles

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