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Dissertation Information for Alexei V. Novikov

NAME:
- Alexei V. Novikov

DEGREE:
- Ph.D.

DISCIPLINE:
- Chemistry

SCHOOL:
- Emory University (USA) (2001)

ADVISORS:
- David Goldsmith

COMMITTEE MEMBERS:
- Albert Padwa
- Lanny S. Liebeskind

MPACT Status: Fully Complete

Title: Part I: Preparation of chiral epoxides and cationic cyclization using chiral sulfenium reagents. Part II: Synthesis of clerodanes: A Diels-Alder approach

Abstract: "The dissertation consists of two parts.

In part I of the dissertation a sequence for preparation of chiral epoxides is studied. The proposed sequence is shown in Figure 1 . An alkene is first reacted with a sulfenyl chloride that carries a chiral auxiliary, and the intermediate is trapped with an acetate. The resulting acetoxysulfide is converted to a sulfonium salt, and then treated with sodium hydroxide to remove the acetate and close the epoxide.*

Two chiral sulfenium reagents were prepared and studied, 1 and 2 ( Figure 2 ).*

Another application of the sulfenyl reagents carrying a chiral auxiliary is also studied--a cationic cyclization initiated by a sulfenyl cation ( Figure 3 ).*

In part II of the dissertation an approach to synthesis of clerodanes is described that resulted in a total synthesis of clerodanes 3 , 4 and 5 .*

The key step of the synthetic approach that is used to construct the trans -fused bicyclic system is Diels-Alder cycloaddition, followed by base equilibration. The short summary of the rest of the final synthetic sequence is shown in Figure 4 .*

*Please refer to dissertation for diagrams."

MPACT Scores for Alexei V. Novikov

A = 0
C = 0
A+C = 0
T = 0
G = 0
W = 0
TD = 0
TA = 0
calculated 2008-04-07 08:12:29

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