Volume 25, Issue 63 p. 14399-14407
Full Paper

Bidirectional Hiyama–Denmark Cross-Coupling Reactions of Bissilyldeca-1,3,5,7,9-pentaenes for the Synthesis of Symmetrical and Non-Symmetrical Carotenoids

Aurea Rivas

Aurea Rivas

Departamento de Química Orgánica, Facultade de Química, CINBIO and IIS Galicia Sur, Universidade de Vigo, 36310 Vigo, Spain

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Víctor Pérez-Revenga

Víctor Pérez-Revenga

Departamento de Química Orgánica, Facultade de Química, CINBIO and IIS Galicia Sur, Universidade de Vigo, 36310 Vigo, Spain

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Prof. Dr. Rosana Alvarez

Corresponding Author

Prof. Dr. Rosana Alvarez

Departamento de Química Orgánica, Facultade de Química, CINBIO and IIS Galicia Sur, Universidade de Vigo, 36310 Vigo, Spain

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Prof. Dr. Angel R. de Lera

Corresponding Author

Prof. Dr. Angel R. de Lera

Departamento de Química Orgánica, Facultade de Química, CINBIO and IIS Galicia Sur, Universidade de Vigo, 36310 Vigo, Spain

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First published: 27 August 2019
Citations: 8

Graphical Abstract

Expanded borders: The Hiyama–Denmark cross-coupling reaction has been extended to the preparation of symmetrical and non-symmetrical carotenoids by using bissilyldeca-1,3,5,7,9-pentaenes.

Abstract

The construction of the carotenoid skeleton by Pd-catalyzed Csp2−Csp2 cross-coupling reactions of symmetrical and non-symmetrical 1,10-bissilyldeca-1,3,5,7,9-pentaenes and the corresponding complementary alkenyl iodides has been developed. Reaction conditions for these bidirectional and orthogonal Hiyama–Denmark cross-coupling reactions of bisfunctionalized pentaenes are mild and the carotenoid products preserve the stereochemical information of the corresponding oligoene partners. The carotenoids synthesized in this manner include β,β-carotene and (3R,3′R)-zeaxanthin (symmetrical) as well as 9-cis-β,β-carotene, 7,8-dihydro-β,β-carotene and β-cryptoxanthin (non-symmetrical).

Conflict of interest

The authors declare no conflict of interest.