alternative access to functionalized 2,8-ethanonoradamantane derivatives
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ID: 138591
2017
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Abstract
7a-(Methoxycarbonyl)-N-methyl-1,3a,5,6,7,7a-hexahydro-4H-1,4,6-(epiethane[1,1,2]triyl)indene-4,9-dicarboximide has been prepared through a modification of a previous synthetic sequence, in which the benzyloxymethyl hydroxyl protecting group has been replaced by methoxymethyl, to avoid the apparent formation of a benzyl ester derivative as a side product. The overall yield of the new synthetic sequence is comparable to the previous one. Two advantages of the new procedure are: (a) no benzyl ester was formed and (b) a stereoisomeric mixture of syn- and anti-alcohols at the beginning of the synthetic sequence could be separated and the rest of the synthesis could be carried out with the main syn-stereoisomer instead of the corresponding stereoisomeric mixture as it was the case in the previous process. Additionally, several functional 2,8-ethanonoradamantane derivatives have been prepared.
| Reference Key |
camps2017moleculesalternative
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|---|---|
| Authors | ;Pelayo Camps;Tània Gómez;Ane Otermin;Mercè Font-Bardia |
| Journal | Journal of ethnopharmacology |
| Year | 2017 |
| DOI |
10.3390/molecules22060906
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| URL | |
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