synthesis of lasofoxifene, nafoxidine and their positional isomers via the novel three-component coupling reaction

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ID: 219129
2010
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Abstract
A Lewis acid-mediated three-component coupling reaction was successfully applied for the synthesis of lasofoxifene (1), nafoxidine (2), and their positional isomers, inv-lasofoxifene (3) and inv-nafoxidine (4). In the presence of HfCl4, the desired one-pot coupling reaction among 4-pivaloyloxybenzaldehyde (5), cinnamyltrimethylsilane (6), and anisole proceeded to afford the corresponding 3,4,4-triaryl-1-butene 7 in high yield. The iodocarbocyclization of the coupling product and the successive elimination of hydrogen iodide forming the olefin part, followed by the migration of the double-bond afforded the common synthetic intermediate of lasofoxifene (1) and nafoxidine (2) via a very concise procedure. Additionally, the syntheses of their positional isomers inv-lasofoxifene (3) and inv-nafoxidine (4) were also achieved through very convenient protocols.
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shiina2010moleculessynthesis Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Isamu Shiina, Kenya Nakata, Yoshiyuki Sano
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Journal Journal of ethnopharmacology
Year 2010
DOI
10.3390/molecules15106773
URL
http://www.mdpi.com/1420-3049/15/10/6773/
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