Studies directed towards the synthesis of bafilomycin A1
Studies directed towards the synthesis of bafilomycin A1
The stereocontrolled synthesis of the C1-C17 fragment 3.1.2 of bafilomycin A1 1.1.1 involved the use of alkoxyallyltin to generate the C14 and C15 stereocenters (C13-C17 fragment 3.1.4), the stereospecific construction of the C10-C11 trisubstituted olefin via organocuprate addition to methyl 2-butynoate and C6-C8 stereotriad construction by nucleophilic cleavage of an epoxy alcohol with lithium dimethylcuprate (C5-C12 fragment 3.1.5). The C10-C12 diene system was created by coupling of 3.1.4 with 3.1.5 by means of a modified Julia olefination reaction. Introduction of the diene functionality at the C5 terminus was followed by lactonisation to afford the C1-C17 fragment 3.1.2 of bafilomycin A1 1.1.1 (Fig 13223).
University of Southampton
1997
Butler, Aoife Patricia
(1997)
Studies directed towards the synthesis of bafilomycin A1.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The stereocontrolled synthesis of the C1-C17 fragment 3.1.2 of bafilomycin A1 1.1.1 involved the use of alkoxyallyltin to generate the C14 and C15 stereocenters (C13-C17 fragment 3.1.4), the stereospecific construction of the C10-C11 trisubstituted olefin via organocuprate addition to methyl 2-butynoate and C6-C8 stereotriad construction by nucleophilic cleavage of an epoxy alcohol with lithium dimethylcuprate (C5-C12 fragment 3.1.5). The C10-C12 diene system was created by coupling of 3.1.4 with 3.1.5 by means of a modified Julia olefination reaction. Introduction of the diene functionality at the C5 terminus was followed by lactonisation to afford the C1-C17 fragment 3.1.2 of bafilomycin A1 1.1.1 (Fig 13223).
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Published date: 1997
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Local EPrints ID: 460243
URI: http://eprints.soton.ac.uk/id/eprint/460243
PURE UUID: 52d2405f-187d-4a9e-80fb-00cf368949bd
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Date deposited: 04 Jul 2022 18:15
Last modified: 04 Jul 2022 18:15
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Author:
Aoife Patricia Butler
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