A key intermediate for the synthesis of Tyromycin A, a C-20 tetrachlorodicarboxylic acid, was produced in six steps starting with a dimerisation of methyl 10-undecenoate which was obtained from a renewable resource, e.g. castor oil. The acyloin condensation product was then oxidised, transformed to the diene, followed by ozonisation, chlorination and finally oxidation to the corresponding tetrachlorodicarboxylic acid.
Undecylenic acid: a valuable renewable Building Block on route to Tyromycin A derivatives / M., Van der Steen; C. V., Stevens; Y., Eeckhout; L., De Buyck; Ghelfi, Franco; Roncaglia, Fabrizio. - In: EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY. - ISSN 1438-9312. - STAMPA. - 110:9(2008), pp. 846-852. [10.1002/ejlt.200800024]
Undecylenic acid: a valuable renewable Building Block on route to Tyromycin A derivatives
GHELFI, Franco;RONCAGLIA, Fabrizio
2008
Abstract
A key intermediate for the synthesis of Tyromycin A, a C-20 tetrachlorodicarboxylic acid, was produced in six steps starting with a dimerisation of methyl 10-undecenoate which was obtained from a renewable resource, e.g. castor oil. The acyloin condensation product was then oxidised, transformed to the diene, followed by ozonisation, chlorination and finally oxidation to the corresponding tetrachlorodicarboxylic acid.
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