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.

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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.
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CHEMISTRY-A EUROPEAN JOURNAL
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11
Zeitschriftennummer
16
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4667-4677
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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.

2 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Novel unit B cryptophycin analogues as payloads for targeted therapy.
Figueras E, Borbély A, Ismail M, Frese M, Sewald N., Beilstein J Org Chem 14(), 2018
PMID: 29977395
Total synthesis and biological evaluation of fluorinated cryptophycins.
Weiß C, Bogner T, Sammet B, Sewald N., Beilstein J Org Chem 8(), 2012
PMID: 23209540

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