Abstract
Reduction of 6/7-carboethoxy-3-phenyltrop-3-en-2-ones with H-2/Pd/C and NaBH4 was studied in order to find a stereoselective route to the corresponding 3-phenyltropan-2-ones and 2alpha/2beta-hydroxy-3-phenyltropanes. The 6/7-exo-carboethoxy-3-phenyltrop-3-en-2ones were selectively reduced by Pd/C to 3beta-phenyltropan-2-ones and 2alpha-hydroxy-3beta-phenyltropanes. The corresponding 2beta-hydroxy-3beta-phenyl analogues were synthesized using NaBH4, with a yield of 40 Reduction of 6-endo-carboethoxy-3-phenyltrop-3-en-2-one yielded several products. The corresponding 7-endo-substituted analogue was selectively reduced with both Pd/C and NaBH4 to 7-endocarboethoxy-3beta-phenyltropin-2-one. Analysis of stereochemically important H-1 NMR spectroscopy parameters was performed for all the products and used for conformational analysis in solution. X-ray analysis was performed for selected compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.
| Original language | English |
|---|---|
| Journal | Tetrahedron |
| Volume | 59 |
| Issue number | 3 |
| Pages (from-to) | 377-383 |
| Number of pages | 7 |
| ISSN | 0040-4020 |
| Publication status | Published - 2003 |
| Externally published | Yes |
| MoE publication type | A1 Journal article-refereed |
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