Synthesis of mono- and dihydroxy-substituted 2-amino-cyclooctanecarboxylic acid enantiomers
(1R,2S,6R)-2-Amino-6-hydroxycyclooctanecarboxylic acid (-)-10 was synthesized from (1R,2S)-2-aminocyclooct-5-enecarboxylic acid (+)-2 via an iodolactone intermediate, while (1R,2S,3R,4S)-2-amino-5,6-dihydroxycyclooctanecarboxylic acid (-)-12 was prepared by using the OsO4-catalysed oxidation of Boc-...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2010
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| Sorozat: | TETRAHEDRON-ASYMMETRY
21 No. 8 |
| doi: | 10.1016/j.tetasy.2010.05.003 |
| mtmt: | 1362104 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/10391 |
| Tartalmi kivonat: | (1R,2S,6R)-2-Amino-6-hydroxycyclooctanecarboxylic acid (-)-10 was synthesized from (1R,2S)-2-aminocyclooct-5-enecarboxylic acid (+)-2 via an iodolactone intermediate, while (1R,2S,3R,4S)-2-amino-5,6-dihydroxycyclooctanecarboxylic acid (-)-12 was prepared by using the OsO4-catalysed oxidation of Boc-protected amino ester (-)-5. The stereochemistry and relative configurations of the synthesized compounds were determined by 1D and 2D NMR spectroscopy (based on 2D NOE cross-peaks and (3)J(H,H) coupling constants) and X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved. |
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| Terjedelem/Fizikai jellemzők: | 957-961 |
| ISSN: | 0957-4166 |