Studies towards lactonamycin : approaches to O-glycoside formation
Please note: Abstract contains images which cannot be displayed. The total synthesis of lactonamycin (1), a natural product isolated from a soil sample, by Matsomoto and co-workers1 is currently under investigation. Lactonamycin (1) possesses antimicrobal activity against Gram-Positive bacteria incl...
Main Author: | |
---|---|
Other Authors: | |
Published: |
Imperial College London
2008
|
Subjects: | |
Online Access: | http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.503161 |
id |
ndltd-bl.uk-oai-ethos.bl.uk-503161 |
---|---|
record_format |
oai_dc |
spelling |
ndltd-bl.uk-oai-ethos.bl.uk-5031612017-08-30T03:18:09ZStudies towards lactonamycin : approaches to O-glycoside formationRzepa, Paula RochaBarrett, Anthony2008Please note: Abstract contains images which cannot be displayed. The total synthesis of lactonamycin (1), a natural product isolated from a soil sample, by Matsomoto and co-workers1 is currently under investigation. Lactonamycin (1) possesses antimicrobal activity against Gram-Positive bacteria including MRSA and VRE as well as appreciable levels of cytotoxicity against tumor cell lines. A highly oxygenated fused perhydrofuran-furanone structural motif and a naphtha[e]isoindole ring system make up the hexacylcic core of lactonamycin (1). Adding to the structural complexity, a 2,3,6-trideoxy sugar unit is connected to the core structure via a highly hindered tertiary glycosidic linkage. Various strategies for glycosidation, using the known ABCD alcohol (±)-2 as a model for the tertiary alcohol of lactonamycin (1) are discussed. Of these include, the use of classical glycosidation approaches and more novel strategies that employ open chain glycosyl donors. In particular, the synthesis of glycoside 4 and subsequent investigations towards target compound 5 are described.615.329Imperial College Londonhttp://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.503161http://hdl.handle.net/10044/1/4254Electronic Thesis or Dissertation |
collection |
NDLTD |
sources |
NDLTD |
topic |
615.329 |
spellingShingle |
615.329 Rzepa, Paula Rocha Studies towards lactonamycin : approaches to O-glycoside formation |
description |
Please note: Abstract contains images which cannot be displayed. The total synthesis of lactonamycin (1), a natural product isolated from a soil sample, by Matsomoto and co-workers1 is currently under investigation. Lactonamycin (1) possesses antimicrobal activity against Gram-Positive bacteria including MRSA and VRE as well as appreciable levels of cytotoxicity against tumor cell lines. A highly oxygenated fused perhydrofuran-furanone structural motif and a naphtha[e]isoindole ring system make up the hexacylcic core of lactonamycin (1). Adding to the structural complexity, a 2,3,6-trideoxy sugar unit is connected to the core structure via a highly hindered tertiary glycosidic linkage. Various strategies for glycosidation, using the known ABCD alcohol (±)-2 as a model for the tertiary alcohol of lactonamycin (1) are discussed. Of these include, the use of classical glycosidation approaches and more novel strategies that employ open chain glycosyl donors. In particular, the synthesis of glycoside 4 and subsequent investigations towards target compound 5 are described. |
author2 |
Barrett, Anthony |
author_facet |
Barrett, Anthony Rzepa, Paula Rocha |
author |
Rzepa, Paula Rocha |
author_sort |
Rzepa, Paula Rocha |
title |
Studies towards lactonamycin : approaches to O-glycoside formation |
title_short |
Studies towards lactonamycin : approaches to O-glycoside formation |
title_full |
Studies towards lactonamycin : approaches to O-glycoside formation |
title_fullStr |
Studies towards lactonamycin : approaches to O-glycoside formation |
title_full_unstemmed |
Studies towards lactonamycin : approaches to O-glycoside formation |
title_sort |
studies towards lactonamycin : approaches to o-glycoside formation |
publisher |
Imperial College London |
publishDate |
2008 |
url |
http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.503161 |
work_keys_str_mv |
AT rzepapaularocha studiestowardslactonamycinapproachestooglycosideformation |
_version_ |
1718521313895645184 |