posted on 2024-01-10, 22:13authored byHolly
E. Bonfield, Colin M. Edge, Marc Reid, Alan R. Kennedy, David D. Pascoe, David M. Lindsay, Damien Valette
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.