Molecular chirality plays a critical role in chemistry, biology, and medicine. To study and better understand conformational chirality, it is necessary to obtain structurally interesting molecules that exhibit this form of chirality. Our lab utilizes total synthesis and methodological development to obtain conformationally chiral natural products of interest. We believe...
The effect of the conjugation with cyclopropyl rings
on the activation parameters for the formation of
carbenes from the corresponding diazo compounds was
investigated using diisopropylcarbene (46), cyclopropyl-isopropylcarbene
(47), and dicyclopropylcarbene (48).
Each of these three carbenes was generated by the
thermolysis of the parent benzenesulfonylhydrazone
potassium salts using DMSO...
Dearomatization reactions exist broadly in biosynthesis and chemical synthesis. The highly functionalized atoms of arenes can be masked by it aromaticity, and upon dearomatization, those reactive atoms can be readily applied to bond formation and further manipulation. The total synthesis of (–)-cephalotaxine and (–)- homoharringtonine is described via an oxidative...
A synthetic approach toward the two major fragments of cathedulin K-19,
euonyminol (4) and dimethyl cathate (69), was investigated. Synthesis of
dimethyl cathate was accomplished in 3 steps starting from 73. Efforts directed
towards the synthesis of euonyminol, a highly oxygenated dihydroagarofuran
sesquiterpene, was advanced to a stage in which...
The photohydrodebromination of brominated paracyclophanes was studied to
help elucidate the possible mechanistic pathways leading to product for
bromoarenes in general. Several brominated [2.2]paracyclophanes were studied to
determine the effect of substitution patterns on this reaction. [2.2]Paracyclophanes
were chosen for this study in order to investigate possible intramolecular excimer
formation...