dc.identifier.uri |
http://dx.doi.org/10.15488/10867 |
|
dc.identifier.uri |
https://www.repo.uni-hannover.de/handle/123456789/10949 |
|
dc.contributor.author |
Nawasreh, Mansour
|
|
dc.contributor.author |
Kirschning, Andreas
|
|
dc.contributor.author |
Duddeck, Helmut
|
|
dc.contributor.author |
Dräger, Gerald
|
|
dc.contributor.author |
Fenske, Dieter
|
|
dc.date.accessioned |
2021-05-03T09:10:21Z |
|
dc.date.available |
2021-05-03T09:10:21Z |
|
dc.date.issued |
2020 |
|
dc.identifier.citation |
Nawasreh, M.; Kirschning, A.; Duddeck, H.; Dräger, G.; Fenske, D.: Novel double functional protection of cephalostatin analogues using a gas-free chlorination method. In: Heliyon 6 (2020), Nr. 1, e03025. DOI: https://doi.org/10.1016/j.heliyon.2019.e03025 |
|
dc.description.abstract |
Herewith, we report on a method that allows to simultaneously protect both the ∆14,15 bond and the carbonyl group of the symmetrical bis-steroidal diketone 2. We found that environmentally friendly and gas-free chlorination is ideally suited to achieve this goal. This method was discovered during our efforts to methoxylate 2 in a solution of dichloromethane and basic methanol in the presence of diacetoxy iodobenzene. Unexpectedly, the ∆14,15 bonds were chlorinated once as well as twice in a statistical manner. Interestingly, the singly dichlorinated desymmetrized product is an ideal precursor for conduction a series of position selective transformations. Importantly, the carbonyl group present in the nonchlorinated hemisphere can be selectively reduced, olefinated or oximated, while the other carbonyl group stays unaltered. A structurally related “monomeric” steroid derivative undergoes ∆14,15 chlorination and 11-position methoxylation under same conditions. These findings represent a powerful entry for preparing new nonsymmetrical cephalostatin derivatives. © 2019 |
eng |
dc.language.iso |
eng |
|
dc.publisher |
London [u.a.] : Elsevier |
|
dc.relation.ispartofseries |
Heliyon 6 (2020), Nr. 1 |
|
dc.rights |
CC BY-NC-ND 4.0 Unported |
|
dc.rights.uri |
https://creativecommons.org/licenses/by-nc-nd/4.0/ |
|
dc.subject |
natural product chemistry |
eng |
dc.subject |
organic chemistry |
eng |
dc.subject |
biochemistry |
eng |
dc.subject |
cancer research |
eng |
dc.subject |
cephalostatin 1 |
eng |
dc.subject |
chemo and regioselective transformations |
eng |
dc.subject |
gas-free chlorination method |
eng |
dc.subject |
double-functional protection |
eng |
dc.subject.ddc |
540 | Chemie
|
|
dc.title |
Novel double functional protection of cephalostatin analogues using a gas-free chlorination method |
|
dc.type |
Article |
|
dc.type |
Text |
|
dc.relation.essn |
2405-8440 |
|
dc.relation.doi |
https://doi.org/10.1016/j.heliyon.2019.e03025 |
|
dc.bibliographicCitation.issue |
1 |
|
dc.bibliographicCitation.volume |
6 |
|
dc.bibliographicCitation.firstPage |
e03025 |
|
dc.description.version |
publishedVersion |
|
tib.accessRights |
frei zug�nglich |
|