Solid phase applications of Dde and the analogue Nde: Synthesis of trypanothione disulphide

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4849-4852

  Kellam, Barrie ^a   Bycroft, Barrie W ^a   Chhabra, Siri Ram ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

SPERMIDINE DERIVATIVE; TRYPANOTHIONE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; SOLID STATE;

EID: 0030979764     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01010-1     Document Type: Article

References (16)

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3. Bannwarth, W.; Huebscher, J.; Barner, R. Bioorg. Med. Chem. Lett., 1996, 6, 1525-1528.
4. Bycroft, B.W.; Chan, W.C.; Hone, N.D.; Millington, S.; Nash, I.A. J. Am. Chem. Soc., 1994, 116, 7415-7416.
5. Nash, I.A.; Bycroft, B.W.; Chan, W.C. Tetrahedron Lett., 1996, 37, 2625-2628.
6. In order to broaden possible applications we have continued to investigate alternative systems related to Dde but based on other available cyclic 1,3-diones; the Nde group is one such example. 2-Acetyl-4-nitroindane-1,3-dione is readily synthesised (Mosher, W.A.; Meier, W.E. J. Org. Chem., 1970, 35, 2924-2926) and reacts with primary amines to give Nde derivatives. A detailed evaluation of Nde as a protecting group will be reported elsewhere. Kellam, B.; Bycroft, B.W.; Chan, W.C.; Chhabra, S.R. in preparation.
7. In order to broaden possible applications we have continued to investigate alternative systems related to Dde but based on other available cyclic 1,3-diones; the Nde group is one such example. 2-Acetyl-4-nitroindane-1,3-dione is readily synthesised (Mosher, W.A.; Meier, W.E. J. Org. Chem., 1970, 35, 2924-2926) and reacts with primary amines to give Nde derivatives. A detailed evaluation of Nde as a protecting group will be reported elsewhere. Kellam, B.; Bycroft, B.W.; Chan, W.C.; Chhabra, S.R. in preparation.
8. Fairlamb, A.H.; Blackburn, P.; Ulrich, P.; Chait, B.T.; Cerami, A. Science, 1985, 227, 1485-1487.
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12. 4 requires m/z 473).
13. 8-Wj-Nde-spermidine is prepared in a similar manner to the corresponding Dde derivative. However because of the unsymmetrical nature of Nde the product is undoubtedly a mixture of geometric isomers. This appears to have no effect on its ability to act as a transient protecting group.
14. Dixit, D.M.; Leznoff, C.C. Isr. J. Chem., 1978, 17, 248-252.
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