The Total Synthesis of Raistrickindole A
Thang Loi Pham, Patcharaporn Sae‐Lao, Hannah Hui Min Toh, Dániel Csókás, Roderick W. Bates
Abstract
The total synthesis of raistrickindole A has been achieved, thereby confirming the proposed structure as an N-hydroxylated DKP. In the first but less selective approach, the DKP was built up by cyclization of a diastereoisomerically mixed N-hydroxylated dipeptide. In the second approach, the same DKP was constructed stereoselectively by the intramolecular Mitsunobu reaction of a hydroxamic acid. The synthesis was completed by a stereoselective oxidative cyclization.
Topics & Concepts
ChemistryDipeptideStereoselectivityMitsunobu reactionTotal synthesisIntramolecular forceStereochemistryHydroxamic acidCombinatorial chemistryOrganic chemistryAmino acidCatalysisBiochemistrySynthetic Organic Chemistry MethodsMicrobial Natural Products and BiosynthesisOxidative Organic Chemistry Reactions