Efficient and versatile stereoselective synthesis of cryptophycins

Mast CA, Eissler S, Stoncius A, Stammler H-G, Neumann B, Sewald N (2005)
CHEMISTRY-A EUROPEAN JOURNAL 11(16): 4667-4677.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
The cryptophycins are a family of cyclic depsipeptides with four retrosynthetic units A to D which correspond to the respective amino acids and hydroxy acids. A new synthetic route to unit A allows the selective generation of all four stereogenic centres by introducing two of them in a catalytic asymmetric dihydroxylation, followed by substrate-controlled diastereoselective reactions. The diol also serves as the epoxide precursor. this approach provides selective access to stereoisomers of unit A (enantiomers, epimers) for structure-activity relationship studies. The unit A derivatives were incorporated into cryptophycin-1, cryptophycin-52 and a novel epimer of cryptophycin-52.
Stichworte
asymmetric synthesis; total synthesis; natural products; antitumor agents; peptides
Erscheinungsjahr
2005
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
11
Ausgabe
16
Seite(n)
4667-4677
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/1602482

Zitieren

Mast CA, Eissler S, Stoncius A, Stammler H-G, Neumann B, Sewald N. Efficient and versatile stereoselective synthesis of cryptophycins. CHEMISTRY-A EUROPEAN JOURNAL. 2005;11(16):4667-4677.
Mast, C. A., Eissler, S., Stoncius, A., Stammler, H. - G., Neumann, B., & Sewald, N. (2005). Efficient and versatile stereoselective synthesis of cryptophycins. CHEMISTRY-A EUROPEAN JOURNAL, 11(16), 4667-4677. doi:10.1002/chem.200500282
Mast, C. A., Eissler, S., Stoncius, A., Stammler, H. - G., Neumann, B., and Sewald, N. (2005). Efficient and versatile stereoselective synthesis of cryptophycins. CHEMISTRY-A EUROPEAN JOURNAL 11, 4667-4677.
Mast, C.A., et al., 2005. Efficient and versatile stereoselective synthesis of cryptophycins. CHEMISTRY-A EUROPEAN JOURNAL, 11(16), p 4667-4677.
C.A. Mast, et al., “Efficient and versatile stereoselective synthesis of cryptophycins”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 11, 2005, pp. 4667-4677.
Mast, C.A., Eissler, S., Stoncius, A., Stammler, H.-G., Neumann, B., Sewald, N.: Efficient and versatile stereoselective synthesis of cryptophycins. CHEMISTRY-A EUROPEAN JOURNAL. 11, 4667-4677 (2005).
Mast, CA, Eissler, S, Stoncius, A, Stammler, Hans-Georg, Neumann, Beate, and Sewald, Norbert. “Efficient and versatile stereoselective synthesis of cryptophycins”. CHEMISTRY-A EUROPEAN JOURNAL 11.16 (2005): 4667-4677.

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