Bidirectional Hiyama–Denmark Cross-Coupling Reactions of Bissilyldeca-1,3,5,7,9-pentaenes for the Synthesis of Symmetrical and Non-Symmetrical Carotenoids |
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Authors: | Aurea Rivas Víctor Pérez-Revenga Prof?Dr Rosana Alvarez Prof?Dr Angel R de Lera |
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Institution: | Departamento de Química Orgánica, Facultade de Química, CINBIO and IIS Galicia Sur, Universidade de Vigo, 36310 Vigo, Spain |
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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). |
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Keywords: | carotenoids cross-coupling Hiyama–Denmark pentaenyl-bis-silanes total synthesis |
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