Studies toward the synthesis of hyperevolutin A : nitrile oxide-allene cycloaddition approach

Author

Dongxiang Zeng

Date of Award

8-2001

Degree Type

Thesis

Degree Name

Master of Science

Major

Chemistry

Major Professor

David G. J. Young

Committee Members

David C. Baker, Ziling Xue

Abstract

This thesis described research conducted on the synthesis of hyperevolutin A—an antitumor antibiotic. An introduction related to the structural and synthetic aspects of polyisoprenylated phloroglucinol natural products is given in section 1. The study investigated an unprecedented intramolecular nitrile oxide-allene approach to a hindered bicyclo[3.3.1] ring system as well as the β,β'-tricarbonyl unit. The research results are summarized in section 2 and described in two separate sections—acyclic model and cyclic model. The acyclic model showed that the β,γ-double bond of the allene is more reactive and this result is attributed to thermodynamic preference. In the cyclic model, the α,β-double bond is more reactive as a result of reversed thermodynamic preference. A functionalized core of hyperevolution A was prepared from 2-methylcyclohexanone in 12 steps in 6% overall yield. All experiments related to this research are summarized in section 3.

Recommended Citation

Zeng, Dongxiang, "Studies toward the synthesis of hyperevolutin A : nitrile oxide-allene cycloaddition approach. " Master's Thesis, University of Tennessee, 2001.
https://trace.tennessee.edu/utk_gradthes/9762