COOEt СООН COOEt (CH,),COOCH (CH,),COOH Ethyl 2-oxocyclo- pentanecarboxylate Br (CH,),COOH (CH,),COOH O (CH,),COOH Nef (CH2),COOCH3 reaction (CH2),COOCH3 n(CH2),COOCH, CH,NO, H aCH),COOCH3 H. 10...


Doxaprost, an orally active bronchodilator patterned after the natural prostaglandins , is synthesized in the following series of reactions starting with ethyl 2-oxocyclopentanecarboxylate. Except for the Nef reaction in Step 8, we have seen examples of all other types of reactions involved in this synthesis.


Q. Describe experimental conditions to bring about Step 7 and account for the fact that the trans isomer is formed in this step.


COOEt<br>СООН<br>COOEt<br>(CH,),COOCH<br>(CH,),COOH<br>Ethyl 2-oxocyclo-<br>pentanecarboxylate<br>Br<br>(CH,),COOH<br>(CH,),COOH O<br>(CH,),COOH<br>Nef<br>(CH2),COOCH3 reaction<br>(CH2),COOCH3<br>n(CH2),COOCH,<br>CH,NO,<br>H<br>aCH),COOCH3<br>H.<br>10<br>(CH2),COOH<br>H<br>(CH),COOH<br>H<br>(CH,),CH3<br>(CH2),CH3<br>(CH,),CH3<br>H.<br>H HƠ CH3<br>Doxaprost<br>(an orally active<br>bronchodilator)<br>

Extracted text: COOEt СООН COOEt (CH,),COOCH (CH,),COOH Ethyl 2-oxocyclo- pentanecarboxylate Br (CH,),COOH (CH,),COOH O (CH,),COOH Nef (CH2),COOCH3 reaction (CH2),COOCH3 n(CH2),COOCH, CH,NO, H aCH),COOCH3 H. 10 (CH2),COOH H (CH),COOH H (CH,),CH3 (CH2),CH3 (CH,),CH3 H. H HƠ CH3 Doxaprost (an orally active bronchodilator)

Jun 10, 2022
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