Synthesis of azasugars. Part 2: Isomerization of polyhydroxylated azepanes

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1613-1616

  Poitout, Lydie ^a   Le Merrer, Yves ^a   Depezay, Jean Claude ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

(1R (6endo, 7exo) 8 oxa 3 azabicyclo 3.2.1 octane 6,7 diol); Azasugar; Azepane; Aziridinium; Isomerization

Indexed keywords

8 OXA 3 AZABICYCLO[3.2.1]OCTANE DERIVATIVE; AZEPINE DERIVATIVE; BICYCLO[3.2.1]OCTANE DERIVATIVE; POLYOL; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029875649     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00097-4     Document Type: Article

References (20)

1. Part of this work was presented at Journées de Chimie Organique 1995, Palaiseau.
2. Part I : see previous paper in this issue.
3. Poitout, L.; Le Merrer, Y.; Depezay, J-C. Tetrahedron Lett. 1994, 35, 3293-3296
4. (a) Johnson, P.Y.; Lisak, J. Tetrahedron Lett. 1975, 3801-3802
5. (b) Sakanow, S.; Haruswa, S.; Yamazaki, N.; Yoneda, R.; Kurhara, T. Chem. Phar. Bull. 1990, 38, 2981-2985.
6. 2Ar with Ar = 1-N-tertbutyloxycarbonyl-indol-3-yl, have been obtained by aminoheterocyclization of 1,2:5,6-dianhydro-3,4-O-dibenzyl-D-mannitol and L-iditol with tryptamine, followed by action of di-tertbutyldicarbonate, according to ref 3. Further utilization of these compounds in the synthesis of non-peptide mimetics of somatostatin will be described elsewhere.
7. (a) Mitsunobu, O. Synthesis 1981, 1-28.
8. (b) Hughes, D.L. Org. React. 1992, 42, 335-395.
9. 13C NMR, MS) in accord with the assigned structure, and satisfactory combustion analysis or accurate mass measurement.
10. Benzoic acid can be replaced by hydrazoic acid to give a mixture of 3-azidoazepane and azidomethyl-piperidine.
11. For analogous thiepanes rearrangement, see : Fuzier, M.; Le Merrer, Y.; Depezay, J-C. Tetrahedron Lett. 1995, 36, 6443-6446.
12. 2,4).
13. Kilonda, A.; Dequeker, E.; Compernolle, F.; Delbeke, P.; Toppet, S.; Babady-Bila; Hoornaert, G.J. Tetrahedron 1995, 51, 849-858.
14. 2,4).
15. The N-ethyl derivative 12, which results from alkylation of 11 by the solvent, was also isolated (55% yield).
16. 2,4).
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