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
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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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