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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.
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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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Publication History
Article published online:
14 April 2023
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