The first total synthesis of the naturally occurring isatisindigoticanine H has been
completed by employing D-mannitol as the chiral pool precursor to install the requisite
stereochemistry of the natural product. Construction of the thiazole unit by dehydrative
cyclization of a α-halo ketone with thiourea followed by Sandmeyer’s reaction and
subsequent nucleophilic addition of lithiated bromothiazole to the Weinreb amide are
the key reactions employed in this regard.
Keywords
Total synthesis - Isatisindigoticanine H - Chiral pool approach - Indothiazinone -
Sandmeyer reaction
