An efficient synthetic method for β-cyclolavandulal and its corresponding alcohol

Mitsunori Oda; Atsushi Isobe; Masashi Hayashi; Ryuta Miyatake; Ichiro Shimao; Shigeyasu Kuroda

doi:10.1002/recl.19961151005

An efficient synthetic method for β-cyclolavandulal and its corresponding alcohol

Mitsunori Oda^*, Atsushi Isobe, Masashi Hayashi, Ryuta Miyatake, Ichiro Shimao, Shigeyasu Kuroda

^*Corresponding author for this work

Center for Environmental Conservation and Research Safety

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

3,3-Dimethylcyclohexanone (5) was efficiently converted to methyl β-cyclolavandulate (6) in 74% yield in three steps, one of which included the preparation of β-methyl α,β-unsaturated esters by coupling lithium dimethylcuprate with enol phosphates of β-oxo esters. Reduction of 6 with LiAlH₄ gave β-cyclolavandulol (2) in 94% yield and oxidation of 2 with pyridinium chlorochromate in the presence of molecular sieves afforded the title aldehyde quantitatively.

Original language	English
Pages (from-to)	438-440
Number of pages	3
Journal	Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands
Volume	115
Issue number	10
DOIs	https://doi.org/10.1002/recl.19961151005
State	Published - 1996/10

ASJC Scopus subject areas

General Chemistry

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title = "An efficient synthetic method for β-cyclolavandulal and its corresponding alcohol",

abstract = "3,3-Dimethylcyclohexanone (5) was efficiently converted to methyl β-cyclolavandulate (6) in 74% yield in three steps, one of which included the preparation of β-methyl α,β-unsaturated esters by coupling lithium dimethylcuprate with enol phosphates of β-oxo esters. Reduction of 6 with LiAlH4 gave β-cyclolavandulol (2) in 94% yield and oxidation of 2 with pyridinium chlorochromate in the presence of molecular sieves afforded the title aldehyde quantitatively.",

author = "Mitsunori Oda and Atsushi Isobe and Masashi Hayashi and Ryuta Miyatake and Ichiro Shimao and Shigeyasu Kuroda",

year = "1996",

month = oct,

doi = "10.1002/recl.19961151005",

language = "英語",

volume = "115",

pages = "438--440",

journal = "Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands",

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T1 - An efficient synthetic method for β-cyclolavandulal and its corresponding alcohol

AU - Oda, Mitsunori

AU - Isobe, Atsushi

AU - Hayashi, Masashi

AU - Miyatake, Ryuta

AU - Shimao, Ichiro

AU - Kuroda, Shigeyasu

PY - 1996/10

Y1 - 1996/10

N2 - 3,3-Dimethylcyclohexanone (5) was efficiently converted to methyl β-cyclolavandulate (6) in 74% yield in three steps, one of which included the preparation of β-methyl α,β-unsaturated esters by coupling lithium dimethylcuprate with enol phosphates of β-oxo esters. Reduction of 6 with LiAlH4 gave β-cyclolavandulol (2) in 94% yield and oxidation of 2 with pyridinium chlorochromate in the presence of molecular sieves afforded the title aldehyde quantitatively.

AB - 3,3-Dimethylcyclohexanone (5) was efficiently converted to methyl β-cyclolavandulate (6) in 74% yield in three steps, one of which included the preparation of β-methyl α,β-unsaturated esters by coupling lithium dimethylcuprate with enol phosphates of β-oxo esters. Reduction of 6 with LiAlH4 gave β-cyclolavandulol (2) in 94% yield and oxidation of 2 with pyridinium chlorochromate in the presence of molecular sieves afforded the title aldehyde quantitatively.

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U2 - 10.1002/recl.19961151005

DO - 10.1002/recl.19961151005

M3 - 学術論文

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SP - 438

EP - 440

JO - Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands

JF - Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands

IS - 10

ER -

An efficient synthetic method for β-cyclolavandulal and its corresponding alcohol

Abstract

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