Total Synthesis of Hydroxy-α- and Hydroxy-β-sanshool Using Suzuki–Miyaura Coupling

Yasushi Igarashi; Katsuyuki Aoki; Hiroaki Nishimura; Isao Morishita; Kimitoshi Usui

doi:10.1248/cpb.c12-00382

Notes

Total Synthesis of Hydroxy-α- and Hydroxy-β-sanshool Using Suzuki–Miyaura Coupling

Yasushi Igarashi, Katsuyuki Aoki, Hiroaki Nishimura, Isao Morishita, Kimitoshi Usui

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Keywords: hydroxy-α-sanshool, hydroxyl-β-sanshool, Suzuki–Miyaura coupling, Zanthoxylum Fruit, Daikenchuto

JOURNAL FREE ACCESS

2012 Volume 60 Issue 8 Pages 1088-1091

DOI https://doi.org/10.1248/cpb.c12-00382

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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.

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