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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,*
Received: 19 December 2013; in revised form: 22 January 2014 / Accepted: 23 January 2014 / Published: 3 February 2014
(This article belongs to the Special Issue Domino Reactions)
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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.

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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.

AMA Style

González-Delgado JA, Escobar G, Arteaga JF, Barrero AF. Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds. Molecules. 2014; 19(2):1748-1762.

Chicago/Turabian Style

González-Delgado, José A.; Escobar, Gustavo; Arteaga, Jesús F.; Barrero, Alejandro F. 2014. "Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds." Molecules 19, no. 2: 1748-1762.


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