A study towards the total synthesis of the pseudopterosins
A study towards the total synthesis of the pseudopterosins
A synthetic approach to the Pseudopterosins, a family of marine natural products which display potent anti-inflammatory and analgesic agents, is described. The approach presented to the pseudopterosins aglycone utilises a tetrahydrofuran derivative and a sequential Friedel-Crafts alkylation reaction. The stereochemistry of the precursor is controlled by iodolactonisation and etherification reactions with kinetic and thermodynamic control of the respective cyclisations. The subsequent cyclisation of the precursor appears to be heavily dependent upon the nature of the side chain in the C-1 position, and treatment of the precursor with boron trifluoride dietherate afforded the desired phenalene nucleus in excellent yield.
University of Southampton
Sibley, Graham Edward Morris
6552b5b7-2ba4-4dd0-ba03-0801a754f30a
2000
Sibley, Graham Edward Morris
6552b5b7-2ba4-4dd0-ba03-0801a754f30a
Sibley, Graham Edward Morris
(2000)
A study 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 which display potent anti-inflammatory and analgesic agents, is described. The approach presented to the pseudopterosins aglycone utilises a tetrahydrofuran derivative and a sequential Friedel-Crafts alkylation reaction. The stereochemistry of the precursor is controlled by iodolactonisation and etherification reactions with kinetic and thermodynamic control of the respective cyclisations. The subsequent cyclisation of the precursor appears to be heavily dependent upon the nature of the side chain in the C-1 position, and treatment of the precursor with boron trifluoride dietherate afforded the desired phenalene nucleus in excellent yield.
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Published date: 2000
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Local EPrints ID: 466957
URI: http://eprints.soton.ac.uk/id/eprint/466957
PURE UUID: a3d9a6c4-556a-4275-8603-c7ab1ffcb0d7
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Date deposited: 05 Jul 2022 08:04
Last modified: 16 Mar 2024 20:53
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Author:
Graham Edward Morris Sibley
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