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![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Atypical Dearomative Spirocyclization of β-Naphthols with Diazoacetamides Using a Silver Catalyst
Haruka Homma1, Shingo Harada1, Tsubasa Ito1
1Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
Abstract:
A chemoselective dearomatization of the less reactive benzenoid unit in β-naphthol was developed. Spirocyclization with a reductant constructs a pivotal structure for drug candidates. One-pot oxidative conversion enabled the tandem dearomatization of β-naphthol, producing conjugated tetraenone variants. The potential utility of the product as an F--selective anion sensor was also demonstrated. Theoretical studies revealed the intermediacy of silver-carbenoid species leading to chemoselective spirocyclization over arene cyclopropanation.
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