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- Title
Aminocyclopentitols from N-Alkylpyridinium Salts: A photochemical approach.
- Authors
Acar, Ersin A.; Glarner, Fabrice; Burger, Ulrich
- Abstract
The photolysis of N-alkylpyridinium halides 9a- e in alkaline H2O gave 6-azabicyclo[3.1.0]hexenol derivatives 10a- e. N-Substituents bearing ether, acetal, and alcohol functions were found to do not adversely influence the photochemical reaction course. The free OH groups of the N-(3-hydroxypropyl) derivative 10d were protected by benzoylation. The ensuing dibenzoate 14 underwent stereocontrolled opening of the aziridine ring on reaction with MeSH/BF3 to give a thioether 15. With benzoic acid in CHCI3, 10d gave the 4-hydroxy-5-aminocyclopent-2-enyl benzoate 11. The meso-2-aminocyclopent-4-ene-1,3-diol 12 was obtained by hydrolysis of 11. On reaction with Boc2O and NaI, the aziridine ring of 14 was converted to a bicyclic compound 17. Hydrolysis of 17 provided the trans-1,3-diol 18, the epimer of 12. Face-selective dihydroxylation of Boc-protected 12 gave a meso-aminocyclopentanetetrol 23 which was characterized upon peracetylation. Dihydroxylation of 15 provided a racemic analogue of epi-mannostatin A ( 26).
- Publication
Helvetica Chimica Acta, 1998, Vol 81, Issue 5-8, p1095
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19980810523