Oligomeric catechins: an enabling synthetic strategy by orthogonal activation and C(8) protection
Ken Ohmori1, Naoko Ushimaru, Keisuke Suzuki
1Department of Chemistry, Tokyo Institute of Technology, and Core Research for Evolutional Science and Technology, Japan Science and Technology Agency, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.
Abstract:
Controlled formation of oligomeric catechins has become possible by an orthogonal synthetic strategy. Bromo-capping of the C(8) position of the flavan skeleton enabled the equimolar coupling of electrophilic and nucleophilic catechin derivatives, enabling an efficient synthetic strategy to complex catechin oligomers.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Cycloaddition Reactions: Overview
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: MO Requirements for Photochemical Activation


