Total synthesis of hydroxy-α- and hydroxy-ß-sanshool using Suzuki-Miyaura coupling.

ABSTRACT

Here, we describe the first total synthesis of hydroxyl-α- and hydroxyl-ß-sanshool, which involves Suzuki-Miyaura coupling (SMC). Hydroxy-α-sanshool (1) was synthesized by SMC of bromoalkyne 4 with boronate 3 followed by (Z)-selective reduction of the triple bond in the coupling product. Hydroxy-ß-sanshool (2) was synthesized by regio- and (E)-selective conversion of 4 to iodoalkene 11 followed by SMC with 3.