The allylic oxidation of tigliane esters.
Fitoterapia
; 148: 104802, 2021 Jan.
Article
em En
| MEDLINE
| ID: mdl-33309651
ABSTRACT
As part of a study on the structure-activity relationships of the anticancer agent tigilanol tiglate (EBC-46, 2), the allylic oxidation of phorbol triacetate (1c) and of the acetonide of its 3αH-dihydroderivative (5) was investigated. The aim was to introduce an oxygen function at C-5 en route to point-like analogues of 2, but functionalization of C-10 was instead observed. This was followed by oxidative fragmentation of ring B to the 9,10-secotigliane derivative 6 and oxidation of the endocyclic Δ6 double bond to the C-6/C-10 oxygen bridged 7-oxotigliane 7. Despite the over-functionalization of ring B, these observations suggest the possibility to modify positions overlooked in the oxidase phase of tigliane biosynthesis and explore novel areas of the phorbol chemical space.
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Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Ésteres de Forbol
/
Antineoplásicos
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article