RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
Synfacts 2023; 19(05): 0433
DOI: 10.1055/s-0042-1752423
DOI: 10.1055/s-0042-1752423
Synthesis of Natural Products
Synthesis of (±)-Ingenol
Winkler JD,
*,
Rouse MB,
Greaney MF,
Harrison SJ,
Jeon YT.
The University of Pennsylvania, Philadelphia, USA
The First Total Synthesis of (±)-Ingenol.
J. Am. Chem. Soc. 2002;
124: 9726-9728
DOI: 10.1021/ja026600a
The First Total Synthesis of (±)-Ingenol.
J. Am. Chem. Soc. 2002;
124: 9726-9728
DOI: 10.1021/ja026600a
Key words
(±)-ingenol - De Mayo reaction - Corey–Posner–Whitesides–House reaction - Upjohn Dihydroxylation - Dess–Martin oxidation - Luche reduction
Significance
Winkler and co-workers report the first total synthesis of (±)-ingenol, a structurally complex and polyoxygenated diterpenoid. Ingenol and its derivatives represent a vital class of natural products which found application in myriads of therapeutic areas inter alia oncology and immunology.
#
Comment
Synthetic endeavors started from enone A and methyl crotonate. The tricyclic core was rapidly assembled in a De Mayo reaction to yield the challenging trans-intrabridgehead stereochemistry. A series of oxidations furnished the desired natural product.
#
#
Publikationsverlauf
Artikel online veröffentlicht:
14. April 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany