Reduction of 6/7-substituted 3-phenyltrop-3-en-2-ones:: stereoselectivity and conformational analysis of the products

被引：5

作者：

Airaksinen, AJ

Lipsonen, J

Ahlgren, M

Vainiotalo, P

Bergström, KA

Laatikainen, R

Vepsäläinen, J

机构：

[1] Univ Kuopio, Dept Chem, FIN-70211 Kuopio, Finland

[2] Univ Joensuu, Dept Chem, FIN-80101 Joensuu, Finland

[3] MAP Med Technol OY, FIN-00251 Helsinki, Finland

来源：

TETRAHEDRON | 2003年 / 59卷 / 03期

关键词：

reduction; NMR; computer-assisted methods; X-ray crystallography; conformation;

D O I：

10.1016/S0040-4020(02)01520-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：377 / 383

页数：7

共 16 条

[1] N-MODIFIED ANALOGS OF COCAINE - SYNTHESIS AND INHIBITION OF BINDING TO THE COCAINE RECEPTOR [J].