Total Syntheses of Xiamycinsâ
A, C, F, H and Oridamycinâ
A and Preliminary Evaluation of their Anti-Fungal Properties.
Angew Chem Int Ed Engl
; 58(43): 15304-15308, 2019 10 21.
Article
in En
| MEDLINE
| ID: mdl-31419367
ABSTRACT
Divergent and enantiospecific total syntheses of the indolosesquiterpenoids xiamycinsâ
A, C, F, H and oridamycinâ
A have been accomplished. The syntheses, which commence from (R)-carvone, employ a key photoinduced benzannulation sequence to forge the carbazole moiety characteristic of these natural products. Late-stage diversification from a common intermediate enabled the first syntheses of xiamycinsâ
C and F, and an unexpected one-pot oxidative decarboxylation, which may prove general, led to xiamycinâ
H. All synthetic intermediates and the natural products were tested for anti-fungal activity. Xiamycinâ
H emerged as an inhibitor of three agriculturally relevant fungal pathogens.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Sesquiterpenes
/
Light
/
Antifungal Agents
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2019
Document type:
Article
Affiliation country:
United States