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

N. Perlman, A. Albeck

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Pages (from-to)4443-4449
Number of pages7
JournalSynthetic Communications
Volume30
Issue number24
DOIs
StatePublished - 2000

Bibliographical note

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

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