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)
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 18E
Related questions
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. Propose a set of experimental conditions to bring about the alkylation in Step 1.
Account for the regioselectivity of the alkylation (i.e., that it takes place on the
carbon between the two carbonyl groups rather than on the other side of the
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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