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

Author

Igarashi Y, Aoki K, Nishimura H, Morishita I, and Usui K

Subjects
Amides chemistry, Magnetic Resonance Spectroscopy, Spectrometry, Mass, Electrospray Ionization, Spectrophotometry, Infrared, Amides chemical synthesis
Abstract

Here, we describe the first total synthesis of hydroxyl-α- and hydroxyl-β-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-β-sanshool (2) was synthesized by regio- and (E)-selective conversion of 4 to iodoalkene 11 followed by SMC with 3.

Published
2012
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