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Synfacts 2023; 19(05): 0433
DOI: 10.1055/s-0042-1752423
Synthesis of Natural Products

Synthesis of (±)-Ingenol

Rezensent(en):
Erick M. Carreira
,
Henrik R. Wilke
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
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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.


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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.


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Publikationsverlauf

Artikel online veröffentlicht:
14. April 2023

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