RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2006(19): 3291-3294
DOI: 10.1055/s-2006-950199
DOI: 10.1055/s-2006-950199
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Use of Nitro Chemistry To Synthesize Unusual Peptides: Application to the Left-Hand Segment of Celogentin C
Weitere Informationen
Received
28 April 2006
Publikationsdatum:
21. August 2006 (online)
Publikationsverlauf
Publikationsdatum:
21. August 2006 (online)
Abstract
A mixed solvent system (diethyl ether-acetonitrile 10:1) was found to permit effective nitration of a complex N-iodoacetyl peptide with silver nitrite.
Key words
peptides - total synthesis - alkyl nitro compounds - solvent effects - nitrations
- 1
Kobayashi J.Suzuki H.Shimbo K.Takeya K.Morita H. J. Org. Chem. 2001, 66: 6626 -
2a
Leung T.-WC.Williams DH.Barna JCJ.Foti S.Oelrichs PB. Tetrahedron 1986, 42: 3333 -
2b
Kahn SD.Booth PM.Waltho JP.Williams DH. J. Org. Chem. 1989, 54: 1901 -
3a
Celogentins A-C, see ref. 1.
-
3b Celogentins D-J, see:
Suzuki H.Morita H.Iwasaki S.Kobayashi J. Tetrahedron 2003, 59: 5307 - 4
Morita H.Shimbo K.Shigemori H.Kobayashi J. Bioorg. Med. Chem. Lett. 2000, 10: 469 ; see also refs 1 and 3 -
5a
Harrison JR.Moody CJ. Tetrahedron Lett. 2003, 44: 5189 -
5b
Comber MF.Moody CJ. Synthesis 1992, 731 -
6a
Bentley DJ.Slawin AMZ.Moody CJ. Org. Lett. 2006, 8: 1975 -
6b
Bentley DJ.Moody CJ. Org. Biomol. Chem. 2004, 2: 3545 - 7
Castle SL.Srikanth GSC. Org. Lett. 2003, 5: 3611 - 8
He L.Yang Y.Castle SL. Org. Lett. 2006, 8: 1165 -
9a
He L.Srikanth GSC.Castle SL. J. Org. Chem. 2005, 70: 8140 -
9b
Srikanth GSC.Castle SL. Org. Lett. 2004, 6: 449 - 10 For a review of radical conjugate additions, see:
Srikanth GSC.Castle SL. Tetrahedron 2005, 61: 10377 -
11a
Mandal M.Yun H.Dudley GB.Lin S.Tan DS.Danishefsky SJ. J. Org. Chem. 2005, 70: 10619 -
11b
Maruyama S.Zhang Y.Wada T.Sasabe H. J. Chem. Soc., Perkin Trans. 1 1999, 41 -
11c
Zhang Y.Wada T.Sasabe H. Tetrahedron Lett. 1996, 37: 5909 - 12
Zen S.Kaji E. Org. Synth. Coll. Vol. VI John Wiley & Sons; London: 1988. p.503 -
13a
Nicolaou KC.Montagnon T.Baran PS.Zhong Y.-L. J. Am. Chem. Soc. 2002, 124: 2245 -
13b
Ito Y.Hirao T.Saegusa T. J. Org. Chem. 1978, 43: 1011 - 14 Attempts to couple N-(nitroacetyl)leucine and valine tert-butyl ester were unsuccesseful. For a rare example of amide bond formation with nitroacetic acid, see:
Huang KS.-L.Lee EH.Olmstead MM.Kurth MJ. J. Org. Chem. 2000, 65: 499 . In this study, the amine was part of an isoxazolidine ring; accordingly, it is presumably less basic than standard amino acid or peptide substrates -
15a
Kornblum N.Ungnade HE. Org. Synth. Coll. Vol. IV John Wiley & Sons; London: 1963. p.724 -
15b
Fenk CJ. Tetrahedron Lett. 1999, 40: 7955 - 16
Endo A.Danishefsky SJ. J. Am. Chem. Soc. 2005, 127: 8298 - 17
Kornblum N.Blackwood RK.Mooberry DD. J. Am. Chem. Soc. 1956, 78: 1501 - 18
Kornblum N.Larson HO.Blackwood RK.Mooberry DD.Oliveto EP.Graham GE. J. Am. Chem. Soc. 1956, 78: 1497 - 19
Crumbie RL.Nimitz JS.Mosher HS. J. Org. Chem. 1982, 47: 4040 - 20
Scardovi N.Casalini A.Peri F.Righi P. Org. Lett. 2002, 4: 965 - 21
Kornblum N.Smiley RA.Blackwood RK.Iffland DC. J. Am. Chem. Soc. 1955, 77: 6269 - 22 For a review, see:
Ono N. The Nitro Group in Organic Synthesis Wiley-VCH; New York: 2001. p.17-20 - 23
Pangborn AB.Giardello MA.Grubbs RH.Rosen RK.Timmers FJ. Organometallics 1996, 15: 1518