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
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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Question
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. Step 9 is done by a Wittig reaction. Suggest a structural formula for a Wittig reagent that gives the product shown

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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