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Synthetic approaches to (1S,3R)-3-aminomethyl-2,2,3-trimethylcyclopentylmethanol and (1S,3R)-3-amino-2,2,3-trimethylcyclopentylmethanol from (+)-camphoric acid

✍ Scribed by María I. Nieto; JoséM. Blanco; Olga Caamaño; Franco Fernández; Generosa Gómez

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 713 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00416-5

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✦ Synopsis

The litle anlinomethyl (5) and amino (6) alcohols, which are of interest as intermediates in the synthesis of carbocyclic analogues of nucleosides, were prepared from (+)-camphoric acid via methyl (1S,3R)-3-carbamoyl-2.3.3-trimelhylcyclopel~tane earboxylale (8). Direct reduction of S 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.

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