Synthesis of (2R,5S)- and (2S,5S)-2-carboxy-1,4-diaza[4.3.0]bicyclononane as building blocks for the synthesis of new potential HIV protease inhibitors

Tetrahedron Asymmetry

Volumn 7, Issue 7, 1996, Pages 1999-2005

  Falorni, Massimo ^a   Porcheddu, Andrea ^a   Giacomelli, Giampaolo ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; PIPERAZINE DERIVATIVE; PROTEINASE INHIBITOR; PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030200959     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00241-8     Document Type: Article

References (14)

1. 1) Thaisrivongs, S. in "Annual Report in Medicinal Chemistry" Bristol, J.A.Ed. Academic Press, Inc., San Diego, CA, 1994, 29, 133-144.
2. 2) Dorsey, B.D.; Levin R.B.; McDaniel, S.L.; Vacca, J.P.; Guare, J.P.; Darke, P.L.; Zugay, J.A.; Emini, E.A.; Schleif, W.A.; Quintero, J.C.; Lin, J.H.; Chen, I.-W.; Holloway, M.K.; Fitzgerald, P.M.D.; Axel, M.G.; Ostovic, D.; Anderson, P.S.; Huff, J.R. J. Med. Chem., 1994, 37, 3443-3451.
3. 3) Falorni, M.; Conti, S.; Giacomelli, G.; Cossu, S.; Soccolini, F. Tetrahedron: Asymmetry, 1995, 6, 287-294.
4. 4) Falorni, M.; Giacomelli, G. Synlett, 1996, 143-144.
5. 5) Ueda, T.; Saito, M.; Kato, T.; Izumya, N. Bull. Chem. Soc. Jpn., 1983, 56, 568-572.
6. 6) The change of the descriptor of the absolute configuration of C-2 on passing from 1b-2b to 1c-2c is only due to the IUPAC nomenclature rules.
7. 7) Powell, J.; James, N.; Smith, S.J. Synthesis, 1986, 338-339.
8. 8) Carlsen, H.J.; Katsuki, T.; Martin, V.S.; Sharpless K.B. J. Org. Chem., 1981, 46, 3936.
9. 3 as catalyst causes the oxidative decomposition of the substrates.
10. 10) The exact characterisation of acids was not possible: some evidences should indicate for these compounds a zwitterionic structure 3: (Equation presented)
11. 11) Shamma, M.; Deno, N.C.; Remar, J.F. Tetrahedron Lett., 1966, 1375.
12. 12) Wilson, N.D.V.; Joule, J.A. Tetrahedron, 1968, 24, 5493-5497.
13. 13) Guttman, St.; Boissonnas, R.A. Helv. Chim. Acta, 1958, 41, 1852-1867.
14. 14) Asami, M.; Ohno, H.; Kobayashi, S.; Mukaiyama, T. Bull. Chem. Soc. Jpn., 1978, 51, 1869-1873.