A Matteson Homologation‐Based Synthesis of Doliculide and Derivatives
Markus Tost, Oliver Andler, Uli Kazmaier
Abstract
Abstract Doliculide belongs to a group of marine cyclodepsipeptides with interesting biological properties. Apart from a halogenated dipeptide, a polyketide fragment containing 5 stereogenic centers is the most eye‐catching element. This building block can be synthesized in a highly stereoselective fashion using only one key reaction: the Matteson homologation. This straightforward protocol allows for the introduction of a wide range of substituents at almost any position of a growing carbon chain and it is therefore perfectly suited for the synthesis of derivatives for structure‐activity relationship studies
Topics & Concepts
StereocenterChemistryPolyketideStereochemistryDipeptideBlock (permutation group theory)PharmacophoreStereoselectivityCombinatorial chemistryEnantioselective synthesisOrganic chemistryCatalysisPeptideCombinatoricsEnzymeBiochemistryBiosynthesisMathematicsSynthetic Organic Chemistry MethodsMarine Sponges and Natural ProductsMicrobial Natural Products and Biosynthesis