A convenient method for the preparation of 20-[18O]-labeled ingenol. Issue 14 (5th April 2017)

• Record Type: Journal Article
• Authors: Pospíšil, Jiří; Béres, Tibor; Strnad, Miroslav
• Is Part Of: Tetrahedron letters. Volume 58:Issue 14(2017)
• Page Start: 1421
• Page End: 1424
• Publication Date: 2017-04-05
• Subjects: Ingenol -- Labeled compounds -- Natural products -- Protecting group-free synthesis -- Mass spectroscopy; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.02.078
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Short and efficient 2 step synthesis of labeled ingenol. Protecting group free introduction of the 18 O atom with excellent selectivity. Highly selective Mitsunobu reaction. 18 O2 -acetic acid as the 18 O atom source. Abstract: A short and efficient protecting group-free synthesis of isotopically labeled 20-[ 18 O]-ingenol has been developed. Based on a highly selective (only one out of four hydroxy groups) Mitsunobu reaction of ingenol with 18 O2 -acetic acid and subsequent methanolysis, this route yielded the desired 20-[ 18 O]-ingenol in high yield and chemical and isotopic purity.