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

Molecules

José A. González-Delgado²  Gustavo Escobar²  Jesús F. Arteaga¹ 

[1] 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;Department of Organic Chemistry and Institute of Biotechnology, University of Granada, Avda Fuentenueva s/n, 18071 Granada, Spain

关键词: trisporoids;    apocarotenoid;    domino reaction;    stereoselective synthesis;   

DOI  :  10.3390/molecules19021748

来源: mdpi

【 摘 要 】

The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a Δ^1,6-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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.