Studies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycin

Studies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycin

Exploitation of the asymmetric electron density at the crown of the oxazolidinone [221] allowed for high diastereofacial selectivity when converting the olefin to an epoxide. Regiocontrolled fragmentation of the epoxide enabled us to introduce the three essential stereocentres of the target alkaloid...

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Main Author: Brann, Paul John
Published: University of Sussex 2013
Subjects:
540
QD0241 Organic chemistry
Online Access:https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.589075
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spelling ndltd-bl.uk-oai-ethos.bl.uk-5890752019-03-05T15:22:14ZStudies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycinBrann, Paul John2013Exploitation of the asymmetric electron density at the crown of the oxazolidinone [221] allowed for high diastereofacial selectivity when converting the olefin to an epoxide. Regiocontrolled fragmentation of the epoxide enabled us to introduce the three essential stereocentres of the target alkaloid (-)-anisomycin [1] both contiguously and with the correct geometry. Installation of the remaining aromatic appendage allowed us to complete the molecular skeleton of the natural product; however, the synthetic step to facilitate this addition reaction also compromised the chiral integrity of the C2 position. Whilst the desired bioactive alkaloid, (-)-anisomycin [1] was not achieved upon completion of the synthesis, construction of the rare stereoisomer, (-)-2-epi-anisomycin [274] in a 9.4% overall yield demonstrates the routes future potential to deliver (-)-anisomycin [1]. For graphics please refer to abstract in pdf540QD0241 Organic chemistryUniversity of Sussexhttps://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.589075http://sro.sussex.ac.uk/id/eprint/47188/Electronic Thesis or Dissertation
collection NDLTD
sources NDLTD
topic 540
QD0241 Organic chemistry
spellingShingle 540
QD0241 Organic chemistry
Brann, Paul John
Studies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycin
description Exploitation of the asymmetric electron density at the crown of the oxazolidinone [221] allowed for high diastereofacial selectivity when converting the olefin to an epoxide. Regiocontrolled fragmentation of the epoxide enabled us to introduce the three essential stereocentres of the target alkaloid (-)-anisomycin [1] both contiguously and with the correct geometry. Installation of the remaining aromatic appendage allowed us to complete the molecular skeleton of the natural product; however, the synthetic step to facilitate this addition reaction also compromised the chiral integrity of the C2 position. Whilst the desired bioactive alkaloid, (-)-anisomycin [1] was not achieved upon completion of the synthesis, construction of the rare stereoisomer, (-)-2-epi-anisomycin [274] in a 9.4% overall yield demonstrates the routes future potential to deliver (-)-anisomycin [1]. For graphics please refer to abstract in pdf
author Brann, Paul John
author_facet Brann, Paul John
author_sort Brann, Paul John
title Studies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycin
title_short Studies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycin
title_full Studies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycin
title_fullStr Studies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycin
title_full_unstemmed Studies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycin
title_sort studies toward the synthesis of (-)-anisomycin : the total synthesis of (-)-2-epi-anisomycin
publisher University of Sussex
publishDate 2013
url https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.589075
work_keys_str_mv AT brannpauljohn studiestowardthesynthesisofanisomycinthetotalsynthesisof2epianisomycin
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