Intramolecular direct dehydrohalide coupling promoted by KO(t)Bu: total synthesis of Amaryllidaceae alkaloids anhydrolycorinone and oxoassoanine.
A transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution (HAS) with aryl radicals has been developed in the presence of potassium tert-butoxide and an organic molecule as the catalyst. The methodology has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), and other related structures. Interestingly, the method also works only in the presence of potassium tert-butoxide.
Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, MP-462023, India.
Subhadip
S
De
Santanu
S
Ghosh
Subhajit
S
Bhunia
Javeed Ahmad
JA
Sheikh
Alakesh
A
Bisai
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000440:Butanols / Q000737:chemistry*; D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry
D047151:Amaryllidaceae Alkaloids; D000440:Butanols; D026121:Indole Alkaloids; D010617:Phenanthridines; C420562:anhydrolycorinone; C512235:oxoassoanine; C077664:tert-butoxide, potassium