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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)

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)

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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. Assuming that the two side chains on the cyclopentanone ring are trans, how many stereoisomers are possible from this synthetic sequence?

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)
Transcribed Image 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)
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