Synthesis of (S)-(-)-β-cuparenone and (S)-(-)-cuparene

Bhasker Reddy Aavula; Qi Cui; Eugene A. Mash

doi:10.1016/S0957-4166(00)00457-2

Synthesis of (S)-(-)-β-cuparenone and (S)-(-)-cuparene

Bhasker Reddy Aavula, Qi Cui, Eugene A. Mash

Chemistry and Biochemistry

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

19 Scopus citations

Abstract

A short and efficient synthesis of the title compounds is described. (S)-(-)-β-Cuparenone was prepared in 31% yield from p-tolualdehyde and mesityl oxide in eight steps. Absolute stereochemistry was established by means of a diastereoselective cyclopropanation using (R,R)-hydrobenzoin as a recoverable auxiliary.

Original language	English (US)
Pages (from-to)	4681-4686
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	11
Issue number	23
DOIs	https://doi.org/10.1016/S0957-4166(00)00457-2
State	Published - Dec 1 2000

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Synthesis of (S)-(-)-β-cuparenone and (S)-(-)-cuparene",

abstract = "A short and efficient synthesis of the title compounds is described. (S)-(-)-β-Cuparenone was prepared in 31% yield from p-tolualdehyde and mesityl oxide in eight steps. Absolute stereochemistry was established by means of a diastereoselective cyclopropanation using (R,R)-hydrobenzoin as a recoverable auxiliary.",

author = "Aavula, {Bhasker Reddy} and Qi Cui and Mash, {Eugene A.}",

note = "Funding Information: Partial support of this work by the University of Arizona through the Materials Characterization Program is gratefully acknowledged. ",

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T1 - Synthesis of (S)-(-)-β-cuparenone and (S)-(-)-cuparene

AU - Aavula, Bhasker Reddy

AU - Cui, Qi

AU - Mash, Eugene A.

N1 - Funding Information: Partial support of this work by the University of Arizona through the Materials Characterization Program is gratefully acknowledged.

PY - 2000/12/1

Y1 - 2000/12/1

N2 - A short and efficient synthesis of the title compounds is described. (S)-(-)-β-Cuparenone was prepared in 31% yield from p-tolualdehyde and mesityl oxide in eight steps. Absolute stereochemistry was established by means of a diastereoselective cyclopropanation using (R,R)-hydrobenzoin as a recoverable auxiliary.

AB - A short and efficient synthesis of the title compounds is described. (S)-(-)-β-Cuparenone was prepared in 31% yield from p-tolualdehyde and mesityl oxide in eight steps. Absolute stereochemistry was established by means of a diastereoselective cyclopropanation using (R,R)-hydrobenzoin as a recoverable auxiliary.

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U2 - 10.1016/S0957-4166(00)00457-2

DO - 10.1016/S0957-4166(00)00457-2

M3 - Article

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 23

ER -

Synthesis of (S)-(-)-β-cuparenone and (S)-(-)-cuparene

Abstract

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