Development of Novel Reactions Using Hypervalent Iodine(III) Reagents: Total Synthesis of Sulfur-Containing Pyrroloiminoquinone Marine Product, (±)-Makaluvamine F
A novel and efficient synthesis of sulfur-containing heterocycles from phenol ethers bearing an alkyl sulfide sidechain using a combined reagent of a hypervalent iodine(III) species and BF3·Et2O is described.
Development of Novel Reactions Using Hypervalent Iodine(III) Reagents: Total Synthesis of Sulfur-Containing Pyrroloiminoquinone Marine Product, (±)-Makaluvamine F
Novel and efficient intramolecular nucleophilic substitution reactions of phenol ethers using activated hypervalent iodine species have been developed and their application to the total synthesis of strongly cytotoxic makaluvamine F (1), a member of sulfur-containing pyrroloiminoquinone marine products, is described.