Efficient and stereospecific synthesis of (z)-Hex-3-enedioic acid, a key intermediate for Gly-Gly cis olefin isostere

N. Perlman; A. Albeck

doi:10.1080/00397910008087071

Efficient and stereospecific synthesis of (z)-Hex-3-enedioic acid, a key intermediate for Gly-Gly cis olefin isostere

N. Perlman, A. Albeck

Department of Chemistry

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13 Scopus citations

Abstract

(z)-Hex-3-enedioic acid, a key intermediate in the synthesis of (z)-5-amino-3-pentenoic acid (a Gly-Gly cis olefin isostere), was synthesized by a short and efficient procedure of sequential oxidations. Thus, selective mono epoxidation of 1,4-cyclohexadiene was followed by periodate oxidation to the appropriate dialdehyde. Finally, Jones oxidation of the dialdehyde afforded the corresponding diacid product.

Original language	English
Pages (from-to)	4443-4449
Number of pages	7
Journal	Synthetic Communications
Volume	30
Issue number	24
DOIs	https://doi.org/10.1080/00397910008087071
State	Published - 2000

Bibliographical note

Funding Information:
Acknowledgment. This work was supported in part by the "Marcus Center

Funding

Acknowledgment. This work was supported in part by the "Marcus Center

Funders	Funder number
Marcus Center

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10.1080/00397910008087071

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AU - Albeck, A.

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PY - 2000

Y1 - 2000

N2 - (z)-Hex-3-enedioic acid, a key intermediate in the synthesis of (z)-5-amino-3-pentenoic acid (a Gly-Gly cis olefin isostere), was synthesized by a short and efficient procedure of sequential oxidations. Thus, selective mono epoxidation of 1,4-cyclohexadiene was followed by periodate oxidation to the appropriate dialdehyde. Finally, Jones oxidation of the dialdehyde afforded the corresponding diacid product.

AB - (z)-Hex-3-enedioic acid, a key intermediate in the synthesis of (z)-5-amino-3-pentenoic acid (a Gly-Gly cis olefin isostere), was synthesized by a short and efficient procedure of sequential oxidations. Thus, selective mono epoxidation of 1,4-cyclohexadiene was followed by periodate oxidation to the appropriate dialdehyde. Finally, Jones oxidation of the dialdehyde afforded the corresponding diacid product.

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Efficient and stereospecific synthesis of (z)-Hex-3-enedioic acid, a key intermediate for Gly-Gly cis olefin isostere

Abstract

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