SYNTHETIC APPROACHES TO )-3-AMINOMETHYL-2,2,3-TRIMETHYLCYCLOPENTYLMETHANOL AND (1S,3R)-3-AMINO-2,2,3-TRIMETHYLCYCLOPENTYLMETHANOL FROM (-CAMPHORIC ACID())

Authors
NIETO MI BLANCO JM CAAMANO O FERNANDEZ F GOMEZ G
Citation
Mi. Nieto et al., SYNTHETIC APPROACHES TO )-3-AMINOMETHYL-2,2,3-TRIMETHYLCYCLOPENTYLMETHANOL AND (1S,3R)-3-AMINO-2,2,3-TRIMETHYLCYCLOPENTYLMETHANOL FROM (-CAMPHORIC ACID()), Tetrahedron, 54(27), 1998, pp. 7819-7830
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
27
Year of publication
1998
Pages
7819 - 7830
Database
ISI
SICI code
0040-4020(1998)54:27<7819:SAT)>2.0.ZU;2-Z
Abstract
The title aminomethyl (5) and amino (6) alcohols, which are of interes t as intermediates in the synthesis of carbocyclic analogues of nucleo sides. were prepared from (+)-camphoric acid via methyl (1S,3R)-3-carb aoyl-2.3.3-trimethylcyclopentane carboxylate (8). Direct reduction of 8 gave 5 in 26% yield. Amino alcohol 6 was prepared in 11-53% overall yields by several approaches, each involving oxidative degradation of 8 followed by a reduction step. (C) 1998 Elsevier Science Ltd. All rig hts reserved.