Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2008(19): 3061-3064
DOI: 10.1055/s-2008-1067252
DOI: 10.1055/s-2008-1067252
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of a Hydroxyethylene Dipeptide Isostere, a Core Unit of the HIV Protease Inhibitors Ritonavir and Lopinavir, and Its C-5 Epimer
Further Information
Received
14 May 2008
Publication Date:
04 September 2008 (online)
Publication History
Publication Date:
04 September 2008 (online)
![](https://www.thieme-connect.de/media/synthesis/200819/lookinside/thumbnails/10.1055-s-2008-1067252-1.jpg)
Abstract
A short synthesis of a hydroxyethylene dipeptide isostere, a core unit of the HIV protease inhibitors ritonavir and lopinavir, and its C-5 epimer is described.
Key words
HIV-AIDS - peptidomimetic aspartyl protease inhibitors - regioselective epoxide opening
-
1a
Cihlar T.Bischofberger N. Annu. Rep. Med. Chem. 2000, 35: 177 -
1b
Martin JA. Antiviral Res. 1992, 17: 265 -
1c
Norbeck DW.Kempf DJ. Annu. Rep. Med. Chem. 1991, 26: 141 -
2a
Kempf DJ.Sham HL.Marsh KC.Flentge CA.Betebenner D.Green BE.McDonald E.Vasavanonda S.Saldivar A.Wideburg NE.Kati WM.Ruiz L.Zhao C.Fino L.Patterson J.Molla A.Plattner JJ.Norbeck DW. J. Med. Chem. 1998, 41: 602 -
2b
Kempf DJ.Marsh KC.Denissen JF.McDonald E.Vasavanonda S.Flentge CA.Green BE.Fino L.Park CH.Kong XP.Plattner J. J.Leonard JM.Norbeck DW.Wideburg NE.Saldivar A.Ruiz L.Kati WM.Sham HL.Robins T.Stewart KD.Hsu A. Proc. Natl. Acad. Sci. U.S.A. 1995, 92: 2484 -
3a
Stoner EJ.Cooper AJ.Dickman DA.Kolaczkowski L.Lallaman JE.Liu J.-H.Oliver-Shaffer PA.Patel KM.Paterson JB.Plata DJ.Riley DA.Sham HL.Stengel PJ.Tien J.-HJ. Org. Process Res. Dev. 2000, 4: 264 -
3b
Sham HL.Kempf DJ.Molla A.Marsh KC.Kumar GN.Chen CM.Kati WM.Stewart K.Lal R.Hsu A.Betebenner D.Korneyeva M.Vasavanonda S.McDonald E.Saldivar A.Wideburg NE.Chen X.Niu P.Park C.Jayanti V.Grabowski B.Granneman GR.Sun E.Japour AJ.Leonard JM.Plattner J.Norbeck DW. Antimicrob. Agents Chemother. 1998, 42: 3218 -
4a
Adamo I.Benedetti F.Berti F.Campaner P. Org. Lett. 2006, 8: 51 -
4b
Tossi A.Benedetti F.Norbedo S.Skrbec D.Berti F.Romeo D. Bioorg. Med. Chem. 2003, 11: 4719 -
4c
Benedetti F.Berti F.Norbedo S. J. Org. Chem. 2002, 67: 8635 -
4d
Ghosh AK.Bilcer G.Schiltz G. Synthesis 2001, 2203 -
4e
Benedetti F.Norbedo S. Chem. Commun. 2001, 203 -
4f
Ghosh AK.Shin D.Mathivanan P. Chem. Commun. 1999, 1025 -
4g
Haight AR.Stuk TL.Allen MS.Bhagavatula L.Fitzgerald M.Hannick SM.Kerdesky FAJ.Menzia JA.Parekh SI.Robbins TA.Scarpetti D.Tien J.-HJ. Org. Process Res. Dev. 1999, 3: 94 -
4h
Gurjar MK.Pal S.Rao AVR.Pariza RJ.Chorgade MS. Tetrahedron 1997, 53: 4769 -
4i
Stuk TL.Haight AR.Scarpetti D.Allen MS.Menzia JA.Robbins TA.Parekh SI.Langridge DC.Tien J.-HJ.Pariza RJ.Kerdesky FAJ. J. Org. Chem. 1994, 59: 4040 -
4j
Kempf DJ.Marsh KC.Codacovi Fino L.Bryant P.Craig-Kennard A.Sham HL.Zhao C.Vasavanonda S.Kohlbrenner WE.Wideburg NE.Saldivar A.Green BE.Herrin T.Norbeck DW. Bioorg. Med. Chem. 1994, 2: 847 -
4k
Ghosh AK.McKee SP.Thompson WJ.Darke PL.Zugay JC. J. Org. Chem. 1993, 58: 1025 -
4l
Baker WR.Pratt JK. Tetrahedron 1993, 49: 8739 - 5
Takano S.Kurotaki A.Takahashi M.Ogasawara K. Synthesis 1986, 403 -
6a
Yadav JS.Srinivas Ch. Tetrahedron Lett. 2002, 43: 3837 -
6b
Chattopadhyay A. J. Org. Chem. 1996, 61: 6104