Novel Fragmentation Reaction of Correolide

Novel Fragmentation Reaction of Correolide

Pentacyclic triterpenoid natural product correolide (1) was converted to ketone 2 via ozonolysis. An unusual fragmentation reaction of ketone 2 with LiCl was discovered. This reaction is general among several similar substrates examined and appears to be specific for the correolide-type E-ring struc...

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Veröffentlicht in:Organic letters 2002-05, Vol.4 (11), p.1871-1873
Hauptverfasser: Bao, Jianming, Baker, Robert K, Doss, George A, Kayser, Frank, Kotliar, Andrew, Miao, Shouwu, Parsons, William H, Rupprecht, Kathleen M
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container_end_page 1873
container_issue 11
container_start_page 1871
container_title Organic letters
container_volume 4
creator Bao, Jianming
Baker, Robert K
Doss, George A
Kayser, Frank
Kotliar, Andrew
Miao, Shouwu
Parsons, William H
Rupprecht, Kathleen M
description Pentacyclic triterpenoid natural product correolide (1) was converted to ketone 2 via ozonolysis. An unusual fragmentation reaction of ketone 2 with LiCl was discovered. This reaction is general among several similar substrates examined and appears to be specific for the correolide-type E-ring structure (ketone). A mechanism involving a retroaldol reaction, a nucleophilic opening of the epoxide, and a subsequent acetoxy elimination reaction was proposed.
doi_str_mv 10.1021/ol020053g
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title Novel Fragmentation Reaction of Correolide
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