Muscone synthesis is possible via an intramolecular Prins reaction. The starting point is cyclododecatriene, which his subjected topartial ozonolysis.With one aldehyde group protected,the other is reacted with isobutenyl magnesium chloride, and the protecting group is hydrolysed off. Then follows what is formally a Prins reaction,and etherification results in cyclisation to the bicyclic dihydropyran. Hydrogenation (at high T) finally gives racemic muscone. a. What is the protective group used in the muscone synthesis above? b. What is the name of the reagent used as the protecting group? c. What groups are protected in the above muscone synthesis ?

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Muscone synthesis is possible via an intramolecular Prins reaction. The starting point is cyclododecatriene, which his subjected topartial ozonolysis.With one aldehyde group protected,the other is reacted with isobutenyl magnesium chloride, and the protecting group is hydrolysed off. Then follows what is formally a Prins reaction,and etherification results in cyclisation to the bicyclic dihydropyran. Hydrogenation (at high T) finally gives racemic muscone. a. What is the protective group used in the muscone synthesis above? b. What is the name of the reagent used as the protecting group? c. What groups are protected in the above muscone synthesis ?
85%
Cyclododecatriene
OH
com
он
TSOH
rac. Muscone
Pt/H
270 °C
90%
НО ОН
75%
OH
OH
MgC
95%
- НО
75%
Transcribed Image Text:85% Cyclododecatriene OH com он TSOH rac. Muscone Pt/H 270 °C 90% НО ОН 75% OH OH MgC 95% - НО 75%
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