A facile synthesis of 7-methylenebicyclo[3.3.1]nonan-3-one and its transformation leading to the novel tricyclic system, protoadamantane

Article abstract of DOI:10.1080/00397919608003522

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-catalyzed 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.

Full text of DOI:10.1080/00397919608003522

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Synthetic Communications: An
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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
a
b
Osamu Muraoka , Yalou Wang , Masafumi
a
a
a
Okumura , Saori Nishiura , Genzoh Tanabe
&
c
Takefumi Momose
a
Faculty of Pharmaceutical Sciences Kinki,
University Kowakae, 3-4-1, Higashi-Osaka, Osaka,
5
77, Japan
b
China Pharmaceutical University, No 24 Tong Jia,
Xiang, Nanjing, 210009, China
c
Faculty of Pharmaceutical Sciences, Toyama
Medical and Pharmaceutical University, Sugitani
2630, Toyama, 930-01, Japan
Published online: 15 Aug 2006.
To cite this article: Osamu Muraoka , Yalou Wang , Masafumi Okumura , Saori
Nishiura , Genzoh Tanabe & Takefumi Momose (1996) A Facile Synthesis of 7-
Methylenebicyclo-[3.3.1]nonan-3-one and its Transformation Leading to the Novel
Tricyclic System, Protoadamantane, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 26:8, 1555-1562,
DOI: 10.1080/00397919608003522

To link to this article: http://dx.doi.org/10.1080/00397919608003522
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