TY  - UNPB
ID  - pittir34492
UR  - http://d-scholarship-dev.library.pitt.edu/34492/
A1  - Hanna, Ramsey
Y1  - 2018/09/27/
N2  - The first ?-boryl ether molecular scaffold for the release of alcohols, aldehydes, and ketones in the presence of H2O2 is described. Utilizing novel chemistry that gives access to ?-hydroxy boronates as well as methods for their successive etherification and acetalization, alcohols, aldehydes, and ketones can be released in vivo in the presence of exogenous and endogenous H2O2.  
The synthesis of potent simplified analogues of Bistramide A, the primary cellular receptor for actin and a potent cytotoxin, have been synthesized in 9 steps, an improvement over the previous total synthesis of Bistramide A (14 steps).  The key step in the synthesis was accomplished using a one pot hetero diels-alder reaction (HDA), 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation, and an acid mediated cyclization.
KW  - Boron
Prodrug
Organic Chemistry
Bistramide
Synthesis
TI  - ?-Boryl Ether Fragmentation via Boronate Oxidation for Cargo Release: The Total Synthesis of Simplified Analogues of Bistramide A
EP  - 245
AV  - public
ER  -