Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids.
J Am Chem Soc
; 143(12): 4732-4740, 2021 03 31.
Article
em En
| MEDLINE
| ID: mdl-33729783
ABSTRACT
Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-ß-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Alcaloides
/
Compostos Heterocíclicos de 4 ou mais Anéis
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2021
Tipo de documento:
Article
País de afiliação:
Estados Unidos