University of Leicester
Browse
U000879.pdf (10.23 MB)

Synthetic approaches to Forskolin.

Download (10.23 MB)
thesis
posted on 2015-11-19, 08:46 authored by Keith A. Menear
In a series of studies directed towards the total synthesis of the natural product forskolin, an intramolecular Diels-Alder approach to the construction of the AB ring system is described, with the stereocontrolled synthesis of the tricyclic adducts (128), (129) and (140). An unusual stereochemical outcome in the intramolecular Diels-Alder reaction of ester (122) to give (129) is also described, and evidence defining the origin of this result considered. Chemical elaboration of the aforementioned tricyclic adducts towards forskolin is presented, together with the intramolecular Diels-Alder cyclisation of acetylene dienophiles to two further tricyclic adducts (90) and (176), possessing the same relative stereochemistry as centres 10a and 10b in forskolin. Finally, the synthesis is extended to include a complementary intermolecular Diels-Alder route to the AB ring system of forskolin, providing an insight into the chemistry of these important decalin intermediates in an approach to the synthesis of forskolin.

History

Date of award

1987-01-01

Author affiliation

Chemistry

Awarding institution

University of Leicester

Qualification level

  • Doctoral

Qualification name

  • PhD

Language

en

Usage metrics

    University of Leicester Theses

    Categories

    No categories selected

    Keywords

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC