A Facile Synthesis of 7-Methylenebicyclo-[3.3.1]nonan-3-one and its Transformation Leading to the Novel Tricyclic System, Protoadamantane

Osamu Muraoka Faculty of Pharmaceutical Sciences Kinki, University Kowakae, 3-4-1, Higashi-Osaka, Osaka, 577, Japan

Yalou Wang China Pharmaceutical University, No 24 Tong Jia, Xiang, Nanjing, 210009, China

Masafumi Okumura Faculty of Pharmaceutical Sciences Kinki, University Kowakae, 3-4-1, Higashi-Osaka, Osaka, 577, Japan

Saori Nishiura Faculty of Pharmaceutical Sciences Kinki, University Kowakae, 3-4-1, Higashi-Osaka, Osaka, 577, Japan

Genzoh Tanabe Faculty of Pharmaceutical Sciences Kinki, University Kowakae, 3-4-1, Higashi-Osaka, Osaka, 577, Japan

Takefumi Momose Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Sugitani 2630, Toyama, 930-01, Japan

Abstract

A practical synthesis of 7-methylenebicyclo[3.3.1]nonan-3-one 2 by the fragmentation of 1,3-adamantanediol 8, which was prepared effectively by the ruthenium-catalized oxyfunctionalization of 1-adamantanol 7, is described. Characteristic transannular cyclization of 2 leading to a novel tricyclic system, 1-hydroxy-4-protoadamantanone 9, via the corresponding exo-epoxide 10 is also presented.

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A Facile Synthesis of 7-Methylenebicyclo-[3.3.1]nonan-3-one and its Transformation Leading to the Novel Tricyclic System, Protoadamantane

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A Facile Synthesis of 7-Methylenebicyclo-[3.3.1]nonan-3-one and its Transformation Leading to the Novel Tricyclic System, Protoadamantane

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