A step in a synthesis of PGE1 (prostanglandin E1, alprostadil) is reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Alprostadil is used as temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.Propose a mechanism for formation of This bromolactone, and account for the observed stereochemistry of each substituent on the cyclohexane ring. Chapter 20: Functional Derivatives of Carboxylic Acids20.35 A step in a synthesis of PGE|, (prostaglandin E1, alprostadil) is reaction of a trisubstitutedcyclohexene with bromine to form a bromolactone. Alprostadil is used as a temporary therapyfor infants born with congenital heart defects that restrict pulmonary blood flow. It bringsabout dilation of the ductus arteriosus, which in turn increases blood flow in the lungs andblood oxygenation.Br„CH,CO,H`CH,CO,H_stepsmany„CO,H+ Br2.o CH,CH,CO,HCH3НОOHA bromolactonePGE,(Alprostadil)Propose a mechanism for formation of this bromolactone, and account for the observed ster-eochemistry of each substituent on the cyclohexane ring.

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Answered: Br CH,CO,H +Br, CH,CO,H CH3 `CH,CO,H…

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Br CH,CO,H +Br, CH,CO,H CH3 `CH,CO,H CH3 A bromolactone

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.58P

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Question

A step in a synthesis of PGE₁(prostanglandin E₁, alprostadil) is reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Alprostadil is used as temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.

Propose a mechanism for formation of This bromolactone, and account for the observed stereochemistry of each substituent on the cyclohexane ring.

Chapter 20: Functional Derivatives of Carboxylic Acids
20.35 A step in a synthesis of PGE|, (prostaglandin E1, alprostadil) is reaction of a trisubstituted
cyclohexene with bromine to form a bromolactone. Alprostadil is used as a temporary therapy
for infants born with congenital heart defects that restrict pulmonary blood flow. It brings
about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and
blood oxygenation.
Br
„CH,CO,H
`CH,CO,H_steps
many
„CO,H
+ Br2.
o CH,
CH,CO,H
CH3
НО
OH
A bromolactone
PGE,
(Alprostadil)
Propose a mechanism for formation of this bromolactone, and account for the observed ster-
eochemistry of each substituent on the cyclohexane ring.

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