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.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor/in
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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.
Stichworte
antitumor agents; depsipeptides; asymmetric synthesis; natural; total synthesis; products
Erscheinungsjahr
2009
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
15
Ausgabe
42
Seite(n)
11273-11287
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/1589822

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.

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