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Synthesis of TMs with a 1,6-Dicarbonyl Pattern

Deprotonation, followed by alkylation with ethyl bromoacetate, provides the required carbon framework. Hydrolysis of both esters, followed by decarboxylation of the P-keto acid moiety, removes the activating group. The resulting carboxyhc acid must be reesterified to give the desired TM. [Pg.175]

Transformation b converts the cyclohexanone alpha carbon to an electrophile by brominating that position. An Sn2 with the stabilized diethyl malonate anion add the required two-carbon chain. As in a, the synthesis of the TM concludes with hydrolysis of the diester, decarboxylation, and reesterification. [Pg.175]

Since attempting to disconnect a 1,6-dicarbonyl leads to illogical synthons, a retrosynthesis involving a functional group interconversion should be considered instead. [Pg.175]

Since ozonolysis of a cyclohexene affords 1,6-dicarbonyls, this would be an effective approach to such target molecules. Use of reductive or oxidative workups can give rise to various combinations of aldehydes, ketones, and carboxylic acids. [Pg.176]

One possible retrosynthesis of a 1,6-dicarbonyl involves a functional group interconversion to a cyclohexene. The cyclohexene derivative can be prepared in a variety of ways (e.g., by a Diels-Alder reaction), so the retrosynthesis can continue from there. The synthesis of target molecules containing six-membered rings will be discussed in a later section. [Pg.176]


See other pages where Synthesis of TMs with a 1,6-Dicarbonyl Pattern is mentioned: [Pg.175]    [Pg.175]   


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