Total Synthesis of Celastrol, Development of a Platform to Access Celastroid Natural Products

Celastroid natural products, triterpenes, have been and continue to be investigated in clinical trials. Celastrol, and for that matter any member of the celastroid family, was prepared for the first time through chemical synthesis starting from 2,3-dimethylbutadiene. A triene cyclization precursor g...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 137; no. 37; pp. 11864 - 11867
Main Authors Camelio, Andrew M, Johnson, Trevor C, Siegel, Dionicio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.09.2015
Amer Chemical Soc
Subjects
Biological Products - chemical synthesis
Biological Products - chemistry
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Triterpenes - chemical synthesis
Triterpenes - chemistry
HEAT-SHOCK
TERPENES
POLYENE CYCLIZATIONS
ALNUSENONE
PENTACYCLIC TRITERPENE
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Summary:Celastroid natural products, triterpenes, have been and continue to be investigated in clinical trials. Celastrol, and for that matter any member of the celastroid family, was prepared for the first time through chemical synthesis starting from 2,3-dimethylbutadiene. A triene cyclization precursor generated in 12 steps underwent a nonbiomimetic polyene cyclization mediated by ferric chloride to generate the generic celastroid pentacyclic core. In the cyclization, engagement of a tetrasubstituted olefin formed adjacent all carbon quaternary centers stereospecifically. With access to the carbocyclic core of the family of natural products, wilforic acid and wilforol A were prepared en route to racemic celastrol.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b06261