Studies into the total synthesis of batrachotoxin
Studies into the total synthesis of batrachotoxin
A stereospecific synthesis of the AB rings of batrachotoxin has been developed. Formation of the silyl enol ether of a 1-keto hexahydroindene was followed by dibromocarbene insertion and `in-situ' ring expansion. Stereoselective attack of the resulting α bromo ketone with lithium acetylide afforded the desired fragment of batrachotoxin. An alternative AB ring synthesis has also been examined, involving a novel carbene mediated ring expansion as its key step. Construction of the C^3-C^9 hemiketal bridge has been considered in some detail. Molecular modelling being used in an attempt to understand the principles governing formation of this linkage. Finally synthetic methodology has also been developed towards the CD rings. 2-Ethynyl-3-methoxycyclopent-2-enone was prepared via a palladium and copper catalysed coupling of 3-ethoxy-2-iodocyclopent-2-enone with (trimethylsilyl)acetylene.
University of Southampton
Pairaudeau, Garry
896e9bfc-e1ad-47ae-b18a-009f69395061
1991
Pairaudeau, Garry
896e9bfc-e1ad-47ae-b18a-009f69395061
Pairaudeau, Garry
(1991)
Studies into the total synthesis of batrachotoxin.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
A stereospecific synthesis of the AB rings of batrachotoxin has been developed. Formation of the silyl enol ether of a 1-keto hexahydroindene was followed by dibromocarbene insertion and `in-situ' ring expansion. Stereoselective attack of the resulting α bromo ketone with lithium acetylide afforded the desired fragment of batrachotoxin. An alternative AB ring synthesis has also been examined, involving a novel carbene mediated ring expansion as its key step. Construction of the C^3-C^9 hemiketal bridge has been considered in some detail. Molecular modelling being used in an attempt to understand the principles governing formation of this linkage. Finally synthetic methodology has also been developed towards the CD rings. 2-Ethynyl-3-methoxycyclopent-2-enone was prepared via a palladium and copper catalysed coupling of 3-ethoxy-2-iodocyclopent-2-enone with (trimethylsilyl)acetylene.
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Published date: 1991
Identifiers
Local EPrints ID: 460637
URI: http://eprints.soton.ac.uk/id/eprint/460637
PURE UUID: eab4cb8c-3044-41bb-a56a-14fdfca4d54f
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Date deposited: 04 Jul 2022 18:26
Last modified: 04 Jul 2022 18:26
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Contributors
Author:
Garry Pairaudeau
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