Conversion of Ketone Trimethylsilylcyanohydrins to Several Types of Compounds

Shunsaku OHTA; Masayuki YAMASHITA; Kazuo ARITA; Takahiro KAJIURA; Ikuo KAWASAKI; Keiko NODA; Michiko IZUMI

doi:10.1248/cpb.43.1294

Shunsaku OHTA, Masayuki YAMASHITA, Kazuo ARITA, Takahiro KAJIURA, Ikuo KAWASAKI, Keiko NODA, Michiko IZUMI

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Keywords: O-trimethylsilylcyanohydrin, MOPAC, Nazarov cyclization, α, β-unsaturated ketone, lactone, tricyclic ketone

JOURNAL FREE ACCESS

1995 Volume 43 Issue 8 Pages 1294-1301

DOI https://doi.org/10.1248/cpb.43.1294

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Abstract

Cyclic ketone O-trimethylsilylcyanohydrins (2) were prepared and converted to various compounds : α-hydroxyketones (3), dehydroxylated ketones (4), α, β-unsaturated ketones (9), tricyclic ketones (10), 1-ethoxycarbonyl-4-phenyl-1, 2, 4a, 5, 6, 7, 8, 8a-octahydro-2-naphthalenone (13), 1-phenylperhydroisocoumarin (18) and 1, 2, 3, 4, 4a, 10, 11, 11a-octahydro-5H-benzo[a, d]cyclohepten-10-one (20).

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