Complex organic transformations, such as the addition of pyrrole to ketene using planar chiral organocatalyst (*PPY), the four-component anhydride- Manniach reactions, and the site-selective desymmetrization of meso-1,2-diol, are remarkable synthetic reactions that provide high yield and high selectivity. However, the exact mechanism and origins of stereocontrol for theses synthetic organic...
This dissertation is separated into two parts according to the two major distinct research projects. In Part I, the full account of synthetic studies toward C10-functionalized lycopodium alkaloids is described. In Part II, the detailed discussion on the exploration of the Pummerer cyclization methodology and its application to the total...
Thermal decomposition of several di-p-toluenesulfonylhydrazones
was studied. It was found that the carbene decomposition
of tetramethyl-1,3-cyclobutanedione, di-p-toluenesulfonylhydrazone
gave two products resulting from
rearrangement. One was identified as 2,5-dimethyl-1,3,4-hexatriene. A tentative structure for the second was
proposed. During the course of the study, a more convenient
procedure for thermal decompositions was...
An improved procedure for the preparation of β-(3-cyclohexenyl) propionic acid from 4-vinylcyclohexene was developed. The
Friedel-Crafts cyclization of β-(3-(3-cyclohexenyl) propionyl chloride
with aluminum chloride was shown to give one bicyclic chlorine
containing ketone in 41% yield. This ketone was identified by a combination of spectral and chemical methods as a...
Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient...