Total synthesis of (+)-sorangicin A.
J Am Chem Soc
; 131(34): 12109-11, 2009 Sep 02.
Article
in En
| MEDLINE
| ID: mdl-19663510
ABSTRACT
The final synthetic challenges associated with (+)-sorangicin A have been overcome, thus leading to the first total synthesis of this complex macrolide antibiotic. Highlights of the highly convergent synthesis include two Julia-Kociénski olefinations to unite three advanced fragments with high E-stereoselectivity. Critical to the final-stage success was the use of a carefully defined Stille coupling and a Mukaiyama macrolactonization as well as Lewis and protic acid-promoted deprotections carefully designed to suppress E/Z isomerization and/or destruction of the delicate (Z,Z,E)-trienoate linkage.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Aminoglycosides
/
Anti-Bacterial Agents
Language:
En
Journal:
J Am Chem Soc
Year:
2009
Document type:
Article
Affiliation country:
United States