Enantioselective Total Synthesis of Mandelalide A and Isomandelalide A: Discovery of a Cytotoxic Ring-Expanded Isomer.
J Am Chem Soc
; 138(3): 770-3, 2016 Jan 27.
Article
in En
| MEDLINE
| ID: mdl-26759923
ABSTRACT
The total synthesis of mandelalide A and its ring-expanded macrolide isomer isomandelalide A has been achieved. Unexpected high levels of cytotoxicity were observed with the ring-expanded isomandelalide A with a rank order of potency mandelalide A > isomandelalide A > mandelalide B. Key aspects of the synthesis include Ag-catalyzed cyclizations (AgCC's) to construct both the THF and THP rings present in the macrocycle, diastereoselective Sharpless dihydroylation of a cis-enyne, and lithium acetylide coupling with a chiral epoxide.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Macrolides
/
Drug Discovery
/
Antineoplastic Agents, Phytogenic
Limits:
Humans
Language:
En
Journal:
J Am Chem Soc
Year:
2016
Document type:
Article