4.4 Article

Application of iron carbonyl complexation to the selective total synthesis of sanshools

Journal

TETRAHEDRON LETTERS
Volume 53, Issue 45, Pages 6000-6003

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.08.135

Keywords

Hydroxyl-alpha-sanshool; Hydroxyl-beta-sanshool; gamma-Sanshool; Iron complex; Zanthoxylum fruit; Daikenchuto

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We focused on the iron-complexes of sanshools (hydroxyl-alpha-sanshool, hydroxyl-beta-sanshool, and gamma-sanshool) as the key intermediates for the selective synthesis of these structurally unstable compounds. Consequently, we developed a concise and selective method for the total synthesis of sanshools in 5-6 steps (26-45% overall yield), including complexation of dienes with iron tricarbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.

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