Gavel Marine, Courant Thibaut, Joosten Antoine Yvan Philippe, Lecourt Thomas
Normandie Univ , INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014 , 76000 Rouen , France.
Org Lett. 2019 Apr 5;21(7):1948-1952. doi: 10.1021/acs.orglett.8b03947. Epub 2019 Mar 8.
A combination of DIBAL-H and CpZrCl is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de- O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.
