Radical cyclisation onto C-3 of 1,6-anhydro-β-D-mannopyranose derivatives. Application to the formation of the C8a centre of (-)-tetrodotoxin

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2745-2748

  Noya, Beatriz ^a   Alonso, Ricardo ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

TETRODOTOXIN;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030907802     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00460-7     Document Type: Article

References (46)

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21. (a) There has recently been an upsurge of interest in 1,6-anhydropyranoses, judging from the number of articles dealing with new methods for their synthesis. See, for example, Léger, S.; Omeara, J.; Wang, Z. Synlett. 1994, 829. Sharma, G. V. M.; Ramanaiah, K. C. V.; Krishnudu, K. Tetrahedron Lett. 1994, 35, 1905. Lauer, G.; Oberdorfer, F. Angew. Chem. Int. Ed. Engl. 1993, 32, 272. Czernecki, S.; Leteux, C.; Veryrières, A. Tetrahedron Lett. 1992, 33, 221.
22. (a) There has recently been an upsurge of interest in 1,6-anhydropyranoses, judging from the number of articles dealing with new methods for their synthesis. See, for example, Léger, S.; Omeara, J.; Wang, Z. Synlett. 1994, 829. Sharma, G. V. M.; Ramanaiah, K. C. V.; Krishnudu, K. Tetrahedron Lett. 1994, 35, 1905. Lauer, G.; Oberdorfer, F. Angew. Chem. Int. Ed. Engl. 1993, 32, 272. Czernecki, S.; Leteux, C.; Veryrières, A. Tetrahedron Lett. 1992, 33, 221.
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38. Although the 1,5-exo cyclization of α-bromoesters was once considered an inferior method of preparation of γ-lactones, it has recently been shown to be a useful method when carried out at high temperature and/or using a low concentration of tin hydride, (a) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
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40. Our experience of the formation and reactivity of C2 esters and acetals of 1,6-anhydro-mannopyranoses suggests that some of them are especially prone to cleavage.
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44. 3SnH and AIBN.
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