Pd-Catalyzed Counter-Steric Site- and Chemoselective Glycosylation: Total Synthesis of Fridamycin A and Himalomycin B
Jihun Kang1, Seungsoo Moon1, Young Ho Rhee1
1Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang 37673, Republic of Korea.
Abstract:
Here, we report a de novo synthetic strategy toward fridamycin-type glycoside natural products. A salient feature of the method is highlighted by the Pd-catalyzed asymmetric hydroalkoxylation of fridamycin A methyl ester with alkoxyallene, which enables site- and chemoselective introduction of 2,3,6-trideoxyglycosysides to various hydroxyl positions in a highly controlled manner. A unique advantage of this method is demonstrated by the total synthesis of himalomycin B and a C4'-epi derivative of the proposed structure of amicenomycin B.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Cycloaddition Reactions: Overview
Alkylation of β-Diester Enolates: Malonic Ester Synthesis


