A convenient method for the preparation of 20-[O-18]-labeled ingenol

0476419 - ÚEB 2018 RIV GB eng J - Journal Article
Pospíšil, Jiří - Béres, T. - Strnad, Miroslav
A convenient method for the preparation of 20-[O-18]-labeled ingenol.
Tetrahedron Letters. Roč. 58, č. 14 (2017), s. 1421-1424. ISSN 0040-4039. E-ISSN 1873-3581
R&D Projects: GA MŠMT(CZ) LO1204
Institutional support: RVO:61389030
Keywords : tandem mass-spectrometry * seed oil * (+)-ingenol * Ingenol * Labeled compounds * Natural products * Protecting group-free synthesis * Mass spectroscopy
OECD category: Organic chemistry
Impact factor: 2.125, year: 2017

A short and efficient protecting groupfree synthesis of isotopically labeled 20-[O-18]-ingenol has been developed. Based on a highly selective (only one out of four hydroxy groups) Mitsunobu reaction of ingenol with O-18(2)acetic acid and subsequent methanolysis, this route yielded the desired 20-[O-18]-ingenol in high yield and chemical and isotopic purity.
Permanent Link: http://hdl.handle.net/11104/0272925