Premium
Photochemical approach to 4,5‐dioxoaporphine alkaloids. The total synthesis of pontevedrine
Author(s) -
Castedo Luis,
Estévez Ramón J.,
Saá José M.,
Suau Rafael
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190613
Subject(s) - chemistry , lactam , alkaloid , total synthesis , transformation (genetics) , stereochemistry , combinatorial chemistry , biochemistry , gene
Abstract An easy and efficient total synthesis of pontevedrine 14b , a 4,5‐dioxoaporphine alkaloid, was achieved for the first time. It is based on the controlled photo‐oxidation of the lactam 7c , to give the benzylidene‐dioxo compound 13b and its subsequent photocyclizaton. A “one pot” transformation of the lactam 7c into norpontevedrine 14a was also achieved.