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
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Mast, CA;
Eissler, S;
Stoncius, A;
Stammler, Hans-GeorgUniBi;
Neumann, BeateUniBi;
Sewald, NorbertUniBi 
Einrichtung
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. https://doi.org/10.1002/chem.200500282
Mast, CA, Eissler, S, Stoncius, A, Stammler, Hans-Georg, Neumann, Beate, and Sewald, Norbert. 2005. “Efficient and versatile stereoselective synthesis of cryptophycins”. Chemistry - A European Journal 11 (16): 4667-4677.
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
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
Weiß C, Bogner T, Sammet B, Sewald N., Beilstein J Org Chem 8(), 2012
PMID: 23209540
28 References
Daten bereitgestellt von Europe PubMed Central.
The cryptophycins: their synthesis and anticancer activity.
Eggen M, Georg GI., Med Res Rev 22(2), 2002
PMID: 11857635
Eggen M, Georg GI., Med Res Rev 22(2), 2002
PMID: 11857635
Schwartz, J. Ind. Microbiol. 5(), 1990
Trimurtulu, J. Am. Chem. Soc. 116(), 1994
Golakoti, J. Am. Chem. Soc. 117(), 1995
AUTHOR UNKNOWN, J. Am. Chem. Soc. 118(), 1996
Three new cryptophycins from Nostoc sp. GSV 224.
Subbaraju GV, Golakoti T, Patterson GM, Moore RE., J. Nat. Prod. 60(3), 1997
PMID: 9090872
Subbaraju GV, Golakoti T, Patterson GM, Moore RE., J. Nat. Prod. 60(3), 1997
PMID: 9090872
Treatment of human prostate tumors PC-3 and TSU-PR1 with standard and investigational agents in SCID mice.
Polin L, Valeriote F, White K, Panchapor C, Pugh S, Knight J, LoRusso P, Hussain M, Liversidge E, Peltier N, Golakoti T, Patterson G, Moore R, Corbett TH., Invest New Drugs 15(2), 1997
PMID: 9220288
Polin L, Valeriote F, White K, Panchapor C, Pugh S, Knight J, LoRusso P, Hussain M, Liversidge E, Peltier N, Golakoti T, Patterson G, Moore R, Corbett TH., Invest New Drugs 15(2), 1997
PMID: 9220288
Discovery of cryptophycin-1 and BCN-183577: examples of strategies and problems in the detection of antitumor activity in mice.
Corbett TH, Valeriote FA, Demchik L, Lowichik N, Polin L, Panchapor C, Pugh S, White K, Kushner J, Rake J, Wentland M, Golakoti T, Hetzel C, Ogino J, Patterson G, Moore R., Invest New Drugs 15(3), 1997
PMID: 9387043
Corbett TH, Valeriote FA, Demchik L, Lowichik N, Polin L, Panchapor C, Pugh S, White K, Kushner J, Rake J, Wentland M, Golakoti T, Hetzel C, Ogino J, Patterson G, Moore R., Invest New Drugs 15(3), 1997
PMID: 9387043
Moore, Curr. Pharm. Des. 2(), 1996
Phase I trial of the cryptophycin analogue LY355703 administered as an intravenous infusion on a day 1 and 8 schedule every 21 days.
Stevenson JP, Sun W, Gallagher M, Johnson R, Vaughn D, Schuchter L, Algazy K, Hahn S, Enas N, Ellis D, Thornton D, O'Dwyer PJ., Clin. Cancer Res. 8(8), 2002
PMID: 12171879
Stevenson JP, Sun W, Gallagher M, Johnson R, Vaughn D, Schuchter L, Algazy K, Hahn S, Enas N, Ellis D, Thornton D, O'Dwyer PJ., Clin. Cancer Res. 8(8), 2002
PMID: 12171879
Cryptophycin: a new antimicrotubule agent active against drug-resistant cells.
Smith CD, Zhang X, Mooberry SL, Patterson GM, Moore RE., Cancer Res. 54(14), 1994
PMID: 7913408
Smith CD, Zhang X, Mooberry SL, Patterson GM, Moore RE., Cancer Res. 54(14), 1994
PMID: 7913408
Tius, Tetrahedron 58(), 2002
Total Synthesis of Cryptophycins via a Chemoenzymatic Approach.
Salamonczyk GM, Han K, Guo Zw , Sih CJ., J. Org. Chem. 61(20), 1996
PMID: 11667584
Salamonczyk GM, Han K, Guo Zw , Sih CJ., J. Org. Chem. 61(20), 1996
PMID: 11667584
White, J. Org. Chem. 64(), 1999
Synthesis of cryptophycin 52 using the Shi epoxidation.
Hoard DW, Moher ED, Martinelli MJ, Norman BH., Org. Lett. 4(10), 2002
PMID: 12000306
Hoard DW, Moher ED, Martinelli MJ, Norman BH., Org. Lett. 4(10), 2002
PMID: 12000306
Synthesis and biological evaluation of cryptophycin analogs with substitution at C-6 (fragment C region).
Varie DL, Shih C, Hay DA, Andis SL, Corbett TH, Gossett LS, Janisse SK, Martinelli MJ, Moher ED, Schultz RM, Toth JE., Bioorg. Med. Chem. Lett. 9(3), 1999
PMID: 10091686
Varie DL, Shih C, Hay DA, Andis SL, Corbett TH, Gossett LS, Janisse SK, Martinelli MJ, Moher ED, Schultz RM, Toth JE., Bioorg. Med. Chem. Lett. 9(3), 1999
PMID: 10091686
Enantiospecific Total Synthesis of the Potent Antitumor Macrolides Cryptophycins 1 and 8.
Gardinier KM, Leahy JW., J. Org. Chem. 62(21), 1997
PMID: 11671811
Gardinier KM, Leahy JW., J. Org. Chem. 62(21), 1997
PMID: 11671811
Pousset, Tetrahedron 57(), 2001
Kolb, Tetrahedron 48(), 1992
Becker, Tetrahedron 51(), 1995
AUTHOR UNKNOWN, 0
Stončius, Tetrahedron: Asymmetry 11(), 2000
Barrow, J. Am. Chem. Soc. 117(), 1995
Matrix metalloproteinase inhibitors containing a (carboxyalkyl)amino zinc ligand: modification of the P1 and P2' residues.
Brown FK, Brown PJ, Bickett DM, Chambers CL, Davies HG, Deaton DN, Drewry D, Foley M, McElroy AB, Gregson M., J. Med. Chem. 37(5), 1994
PMID: 8126708
Brown FK, Brown PJ, Bickett DM, Chambers CL, Davies HG, Deaton DN, Drewry D, Foley M, McElroy AB, Gregson M., J. Med. Chem. 37(5), 1994
PMID: 8126708
Thompson, J. Org. Chem. 46(), 1981
AUTHOR UNKNOWN, 0
Carlsen, J. Org. Chem. 46(), 1981
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 15915529
PubMed | Europe PMC
Suchen in
Google Scholar