Isolation, Structure, and Total Synthesis of the Marine Macrolide Mangrolide D.
Org Lett
; 21(8): 2957-2961, 2019 04 19.
Article
in En
| MEDLINE
| ID: mdl-30957503
ABSTRACT
The isolation, characterization, and total synthesis of the macrocyclic polyene mangrolide D is reported. A 16-step total synthesis relies on robust Suzuki and ring-closing metathesis reactions, and an iron-catalyzed hydroazidation of an exomethylene substituted tetrahydropyran as a key step for the synthesis of the appended 4- epi-vancosamine sugar. Although mangrolide D did not display antibiotic activity, this work should prove enabling toward the synthesis of the antitubercular tiacumicins which display a virtually identical macrocyclic backbone.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Polyenes
/
Macrolides
/
Anti-Bacterial Agents
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2019
Document type:
Article
Affiliation country:
Estados Unidos