Total Synthesis of (+)-Isatisine A

The asymmetric total synthesis or (+)-isatisine A has been accomplished commencing with a Lewis acid-catalyzed cyclization of homochrial (5)-vinylcyclopropane diester and N-tosylindole-2-carboxaldehyde to construct the tetrahydrofuran ring A palladium-catalyzed oxidative decarboxylation was iodized to obtain the dihydrofuran required for the subsequent dihydroxylation reaction to install the (1101 present on the tetrahydrofuran ring The total synthesis was completed by an indole oxidation and electrophilic aromatic substitution sequence to construct isatisine A acetonide winch was then Lamed fof waid to the antipode of the natural product The absolute configuration of the natural enantiomer (-)-isatisine A was determined to be C2(S). C9(R) C10(S) C12(R), and C13(R)