A total synthesis of isosolanone

Article abstract of DOI:10.1080/00397919308011147

Nitroaldol reaction of acetone with nitromethane in the presence of base to give a nitroalcohol 3, followed by acetylation, and subsequent reduction of the resultant acetate 4 with NaBH₄ gave 2-methyl-1 nitropropane 5. Michael reaction of 5 in base with acrylonitrile to give nitronitrile 6, and Nef conversion of the nitro group resulted in the corresponding ketonic nitrile 7. Wittig olefination of the ketonic nitrile with 3-methyl-2-butenyl triphenylphosphonium bromide 8 gave dienenitrile 9, which upon treatment with MeLi, followed by acidic work up, provided isosolanone 2.

Full text of DOI:10.1080/00397919308011147

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Synthetic Communications: An
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A Total Synthesis of Isosolanone
a
a
a
Woo Young Lee , Se Young Jang , Woo Ke Chae
&
b
Oee Sook Park
a
Department of Chemistry, Seoul National
University, Seoul, 151-742, Korea
b
Department of Chemistry, Chungbuk National
University, Chungbuk, 306-763, Korea
Version of record first published: 23 Sep 2006.
To cite this article: Woo Young Lee, Se Young Jang, Woo Ke Chae & Oee Sook Park
(1993): A Total Synthesis of Isosolanone, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 23:21, 3037-3046
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