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Spirobicyclo[2.2.2]octane derivatives: mimetics of baccatin III and paclitaxel (Taxol)

Almqvist, Fredrik ; Manner, Sophie LU ; Thornqvist, Viveca LU ; Berg, Ulf LU ; Wallin, M and Frejd, Torbjörn LU (2004) In Organic and Biomolecular Chemistry 2(21). p.3085-3090
Abstract
The formylated spirobyclic alcohol 8a was computer modeled to be a mimetic of paclitaxel. In this model, the formyl group was used as a truncated paclitaxel side chain in order to reduce the computational work. Compound 8c, carrying the paclitaxel side chain, was synthesized in six steps from optically active 1,3-diketone 12. Microtubule stabilization was not observed for 8c, indicating that the model needs to be adjusted.
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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic and Biomolecular Chemistry
volume
2
issue
21
pages
3085 - 3090
publisher
Royal Society of Chemistry
external identifiers
  • pmid:15505712
  • wos:000224703400008
  • scopus:9144227035
  • pmid:15505712
ISSN
1477-0539
DOI
10.1039/B409678A
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
b08553d3-68fb-4503-8351-4e143f0d7cf3 (old id 139418)
date added to LUP
2016-04-01 11:51:37
date last changed
2025-10-14 10:29:25
@article{b08553d3-68fb-4503-8351-4e143f0d7cf3,
  abstract     = {{The formylated spirobyclic alcohol 8a was computer modeled to be a mimetic of paclitaxel. In this model, the formyl group was used as a truncated paclitaxel side chain in order to reduce the computational work. Compound 8c, carrying the paclitaxel side chain, was synthesized in six steps from optically active 1,3-diketone 12. Microtubule stabilization was not observed for 8c, indicating that the model needs to be adjusted.}},
  author       = {{Almqvist, Fredrik and Manner, Sophie and Thornqvist, Viveca and Berg, Ulf and Wallin, M and Frejd, Torbjörn}},
  issn         = {{1477-0539}},
  language     = {{eng}},
  number       = {{21}},
  pages        = {{3085--3090}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{Organic and Biomolecular Chemistry}},
  title        = {{Spirobicyclo[2.2.2]octane derivatives: mimetics of baccatin III and paclitaxel (Taxol)}},
  url          = {{http://dx.doi.org/10.1039/B409678A}},
  doi          = {{10.1039/B409678A}},
  volume       = {{2}},
  year         = {{2004}},
}