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

Fredrik Almqvist; Sophie Manner; Viveca Thornqvist; Ulf Berg; M Wallin; Torbjörn Frejd

doi:10.1039/B409678A

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

Fredrik Almqvist, Sophie Manner, Viveca Thornqvist, Ulf Berg, M Wallin, Torbjörn Frejd

Centre for Analysis and Synthesis

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	3085-3090
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	21
DOIs	https://doi.org/10.1039/B409678A
Publication status	Published - 2004

Bibliographical note

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)

Subject classification (UKÄ)

Organic Chemistry

Access to Document

10.1039/B409678A

Cite this

@article{b08553d368fb450383514e143f0d7cf3,

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

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 = "Fredrik Almqvist and Sophie Manner and Viveca Thornqvist and Ulf Berg and M Wallin and Torbj{\"o}rn Frejd",

note = "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)",

year = "2004",

doi = "10.1039/B409678A",

language = "English",

volume = "2",

pages = "3085--3090",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0539",

publisher = "Royal Society of Chemistry",

number = "21",

}

TY - JOUR

T1 - Spirobicyclo[2.2.2]octane derivatives: mimetics of baccatin III and paclitaxel (Taxol)

AU - Almqvist, Fredrik

AU - Manner, Sophie

AU - Thornqvist, Viveca

AU - Berg, Ulf

AU - Wallin, M

AU - Frejd, Torbjörn

N1 - 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)

PY - 2004

Y1 - 2004

N2 - 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.

AB - 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.

U2 - 10.1039/B409678A

DO - 10.1039/B409678A

M3 - Article

C2 - 15505712

SN - 1477-0539

VL - 2

SP - 3085

EP - 3090

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 21

ER -

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

Abstract

Bibliographical note

Subject classification (UKÄ)

Access to Document

Fingerprint

Cite this