A5044338223- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Crystallography and molecular interactions
- Catalytic C–H Functionalization Methods
- Synthesis and Catalytic Reactions
- Synthetic Organic Chemistry Methods
- Catalytic Alkyne Reactions
- Natural product bioactivities and synthesis
- Cancer Treatment and Pharmacology
- Cyclopropane Reaction Mechanisms
- Traditional and Medicinal Uses of Annonaceae
- Asymmetric Hydrogenation and Catalysis
- Oxidative Organic Chemistry Reactions
- Marine Sponges and Natural Products
- Radical Photochemical Reactions
- Asymmetric Synthesis and Catalysis
University of California, Berkeley
2020-2024
Korea Advanced Institute of Science and Technology
2017
Saturated cyclic amines (aza-cycles) are ubiquitous structural motifs found in pharmaceuticals, agrochemicals, and bioactive natural products. Given their importance, methods that directly functionalize aza-cycles high demand. Herein, we disclose a fundamentally different approach to functionalizing which relies on C–C cleavage attendant cross-coupling. The initial functionalization step is the generation of underexplored N-fused bicyclo α-hydroxy-β-lactams under mild, visible light...
Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H C-C bond functionalizations. Inspired by Norrish-Yang Type II reaction, functionalization azacycles is achieved forming α-hydroxy-β-lactams precursor α-ketoamide derivatives under mild, visible light conditions. Selective cleavage distal C(sp
Chemical synthesis of natural products is typically inspired by the structure and function a target molecule. When both factors are interest, such as in case taxane diterpenoids, can serve platform for synthetic strategy development enable new biological exploration. Guided this paradigm, we present here unified enantiospecific approach to diverse cores from feedstock monoterpenoid (S)-carvone. Key success our was use skeletal remodeling which began with divergent reorganization convergent...
The construction of complex aza-cycles is interest to drug discovery due the prevalence nitrogen-containing heterocycles in pharmaceutical agents. Herein we report an intramolecular C-H amination approach afford value-added and complexity-enriched bridged bicyclic amines. Guided by density functional theory nuclear magnetic resonance investigations, determined unique roles light heat activation bicyclization mechanism. We applied both a synergistic fashion, achieving gram-scale aza-cycle synthesis.
Abstract An enantio‐ and stereoselective formal total synthesis of (+)‐frondosin A was accomplished through an oxidopyrylium‐ion‐mediated [5+2] cycloaddition reaction. The reaction provided not only efficient way constructing the frondosin skeleton but also facial discrimination ether bridge for complete control relative stereochemistry substituents in A.
Herein, we describe the synthesis of substituted oxepane derivatives through skeletal remodeling 4-hydroxy-2-cyclobutenones, which are readily prepared from commercially available dialkyl squarates upon their reaction with acrylonitrile. Mechanistically, a Rh(I)-catalyzed C-C bond formation and cleavage cascade is proposed. Specifically, fused [3.2.0] bicycle proposed to form squarate-derived cyclobutenols via an unusual intermolecular oxa-Michael addition tertiary alcohol acrylonitrile,...