Synthesis of 2,6-trans-tetrahydropyrans using a palladium-catalyzed oxidative heck redox-relay strategy

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Bonfield, Holly E. and Edge, Colin M. and Reid, Marc and Kennedy, Alan R. and Pascoe, David D. and Lindsay, David M. and Valette, Damien (2024) Synthesis of 2,6-trans-tetrahydropyrans using a palladium-catalyzed oxidative heck redox-relay strategy. Organic Letters, 26 (14). pp. 2857-2861. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.3c03866)

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Abstract

The C-aryl-tetrahydropyran motif is prevalent in nature in a number of natural products with biological activity; however, this challenging architecture still requires novel synthetic approaches. We demonstrate the application of a stereoselective Heck redox-relay strategy for the synthesis of functionalized 2,6-trans-tetrahydropyrans in excellent selectivity in a single step from an enantiopure dihydropyranyl alcohol, proceeding through a novel exo-cyclic migration. The strategy has also been applied to the total synthesis of a trans-epimer of the natural product centrolobine in excellent yield and stereoselectivity.

ORCID iDs

Bonfield, Holly E., Edge, Colin M., Reid, Marc ORCID logoORCID: https://orcid.org/0000-0003-4394-3132, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Pascoe, David D., Lindsay, David M. ORCID logoORCID: https://orcid.org/0000-0003-4498-5094 and Valette, Damien;
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