Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues

Eissler S, Bogner T, Nahrwold M, Sewald N (2009)
CHEMISTRY-A EUROPEAN JOURNAL 15(42): 11273-11287.

Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Autor
; ; ;
Abstract / Bemerkung
Cryptophycins are a family of highly cytotoxic, cyclic depsipeptides. They display antitumour activity that is largely maintained for multidrug-resistant tumour cells. Cryptophycins are composed of four building blocks (units A-D) that correspond to the respective amino and hydroxy acids. A new synthetic route to unit A allows the selective generation of all four stereogenic centres in a short, efficient and reliable synthesis and contributes to an easier and faster synthesis of cryptophycins. The first two stereogenic centres are introduced by a catalytic asymmetric dihydroxylation, whereas the remaining two stereogenic centres are introduced with substrate control of diastercoselectivity. The stereogenic diol function also serves as the epoxide precursor. The approach was used to synthesise the native unit A building block as well as three para-alkoxymethyl analogues from which cryptophycin-52 and three analogous cryptophycins were prepared. Macrocyclisation of the seco-depsipeptides was based on ring-closing metathesis.
Erscheinungsjahr
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
15
Zeitschriftennummer
42
Seite
11273-11287
ISSN
eISSN
PUB-ID

Zitieren

Eissler S, Bogner T, Nahrwold M, Sewald N. Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL. 2009;15(42):11273-11287.
Eissler, S., Bogner, T., Nahrwold, M., & Sewald, N. (2009). Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL, 15(42), 11273-11287. doi:10.1002/chem.200901750
Eissler, S., Bogner, T., Nahrwold, M., and Sewald, N. (2009). Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL 15, 11273-11287.
Eissler, S., et al., 2009. Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL, 15(42), p 11273-11287.
S. Eissler, et al., “Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 15, 2009, pp. 11273-11287.
Eissler, S., Bogner, T., Nahrwold, M., Sewald, N.: Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues. CHEMISTRY-A EUROPEAN JOURNAL. 15, 11273-11287 (2009).
Eissler, Stefan, Bogner, Tobias, Nahrwold, Markus, and Sewald, Norbert. “Efficient Synthesis of Cryptophycin-52 and Novel para-Alkoxymethyl Unit A Analogues”. CHEMISTRY-A EUROPEAN JOURNAL 15.42 (2009): 11273-11287.

3 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting.
Weiss C, Figueras E, Borbely AN, Sewald N., J Pept Sci 23(7-8), 2017
PMID: 28661555
Drugs that target dynamic microtubules: a new molecular perspective.
Stanton RA, Gernert KM, Nettles JH, Aneja R., Med Res Rev 31(3), 2011
PMID: 21381049
New microtubule-inhibiting anticancer agents.
Chen SM, Meng LH, Ding J., Expert Opin Investig Drugs 19(3), 2010
PMID: 20141350

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 19760734
PubMed | Europe PMC

Suchen in

Google Scholar