TY  - JOUR
ID  - pittir25623
UR  - http://d-scholarship-dev.library.pitt.edu/25623/
IS  - 14
A1  - Wipf, P
A1  - Coish, PDG
Y1  - 1999/07/09/
N2  - We have developed a highly convergent synthesis of the manumycin-type m- C7N-antibiotic nisamycin that is applicable to other members of this family of antibiotics. The synthesis features a three-step sequence to the epoxyquinol core that serves as a scaffold for the attachment of the polyene side chains. The eastern polyene side chain was constructed via a novel organozirconocene-mediated synthesis. Zirconocene methodology was also applied to the synthesis of the polyene side chains of asukamycin. The southern side chain of nisamycin was introduced via a Stille reaction that employed a vinyl bromo ketone, derived from an acid-sensitive bromo ketal. Pd-mediated coupling of the vinyl bromide with a stannyl TIPS ester gave TIPS-protected nisamycin that was readily converted to the natural product.
JF  - Journal of Organic Chemistry
VL  - 64
SN  - 0022-3263
TI  - Total synthesis of (±)-nisamycin
SP  - 5053 
AV  - public
EP  -  5061
ER  -