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Synthesis of (12,13-13C2)retinal and (13,1413C2)retinal: A strategy to prepare multiple-13C-labeled conjugated systems

✍ Scribed by M. Groesbeek; G. A. Rood; J. Lugtenburg

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 665 KB
Volume: 111
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19921110307

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✦ Synopsis

Abstract

(12,13‐^13^C~2~)Retinal, (13,14‐^13^C~2~)retinal, (19‐^13^C)retinal and (20‐^13^C)retinal (1) were prepared in a simple fashion in high yield via a consecutive strategy. The key step is the reaction of a N‐methoxy‐N‐methylamide with an alkyllithium or a Grignard reagent. The preparation of the required N‐methoxy‐N‐methylamide is discussed. In this scheme, only three commercially available ^13^C‐labeled starting materials (ethyl bromoacetate, acetonitrile and methyl iodide) are sufficient to construct retinals with any possible combination of ^13^C labeling in the conjugated tail end. This strategy is applicable to the preparation of many other conjugated systems, such as retinoids, carotenoids and polyenes.

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