Towards the total synthesis of the pseudopterosins
Towards the total synthesis of the pseudopterosins
A synthetic approach to the pseudopterosins, a family of marine natural products shown to be potent anti-inflammatory and analgesic agents has been investigated. The key steps in this approach involve either a Lewis acid mediated Friedel-Crafts alkylation of an epoxide tethered to an arene to give a bicyclic precursor to pseudopterosin or a Brønstead-Lowry acid mediated alkylation reaction of a γ-methylene-γ-butyrolactone to give a benzylic spirofuranone. Hydrogenation then exposure to a Brønstead-Lowry acid gives a phenalene skeleton related to pseudopterosin. The scope and limitation of the reactions has been investigated in several model systems.
This work has demonstrated that the intramolecular alkylation of an arene with a γ-methylene-γ-butyrolactone proceeds with a remarkable degree of diastereoselectivity. This has been attributed to an axially orientated methyl group at C7 in the precursor. Also notable is the control of relative stereochemistry of the C3 and C4 centres via the stereorelay C7→C4→C3.
Previous syntheses of the pseudopterosins including synthetic approaches towards the tricyclic aglycone are reviewed in Chapter 1.
University of Southampton
Wilden, Jonathan David
fcfa61ce-75cd-4b4d-9c29-3c9695dd5742
2000
Wilden, Jonathan David
fcfa61ce-75cd-4b4d-9c29-3c9695dd5742
Wilden, Jonathan David
(2000)
Towards the total synthesis of the pseudopterosins.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
A synthetic approach to the pseudopterosins, a family of marine natural products shown to be potent anti-inflammatory and analgesic agents has been investigated. The key steps in this approach involve either a Lewis acid mediated Friedel-Crafts alkylation of an epoxide tethered to an arene to give a bicyclic precursor to pseudopterosin or a Brønstead-Lowry acid mediated alkylation reaction of a γ-methylene-γ-butyrolactone to give a benzylic spirofuranone. Hydrogenation then exposure to a Brønstead-Lowry acid gives a phenalene skeleton related to pseudopterosin. The scope and limitation of the reactions has been investigated in several model systems.
This work has demonstrated that the intramolecular alkylation of an arene with a γ-methylene-γ-butyrolactone proceeds with a remarkable degree of diastereoselectivity. This has been attributed to an axially orientated methyl group at C7 in the precursor. Also notable is the control of relative stereochemistry of the C3 and C4 centres via the stereorelay C7→C4→C3.
Previous syntheses of the pseudopterosins including synthetic approaches towards the tricyclic aglycone are reviewed in Chapter 1.
Text
772035.pdf
- Version of Record
More information
Published date: 2000
Identifiers
Local EPrints ID: 464296
URI: http://eprints.soton.ac.uk/id/eprint/464296
PURE UUID: e6b12eb6-031c-44df-8c82-e2b24e9f7e18
Catalogue record
Date deposited: 04 Jul 2022 21:59
Last modified: 16 Mar 2024 19:23
Export record
Contributors
Author:
Jonathan David Wilden
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics