Journals / Turkish Journal of Chemistry / 2009 / Cilt: 33 - Sayı: 2

A Mild Method for the Cleavage of Ketals Using IBX

Pages
209–214
DOI
—

Abstract

Investigation on the total synthesis of batrachotoxin 1 revealed that the cyclic ketals could be cleaved to ketone with IBX in DMSO at 70-81 °C under very mild conditions. A variety of functional groups showed no interference under these conditions except vinyl bromides, which, in fact, inhibits the single electron transfer to IBX.

Özet

Investigation on the total synthesis of batrachotoxin 1 revealed that the cyclic ketals could be cleaved to ketone with IBX in DMSO at 70-81 °C under very mild conditions. A variety of functional groups showed no interference under these conditions except vinyl bromides, which, in fact, inhibits the single electron transfer to IBX.

Keywords: Deprotection, ketal, IBX, ketone, single electron transfer, batrachotoxin.