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Molecules 2017, 22(6), 906; doi:10.3390/molecules22060906

Alternative Access to Functionalized 2,8-Ethanonoradamantane Derivatives

1
Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia i Ciències de la Alimentació and Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Joan XXIII 27-31, Barcelona 08028, Spain
2
Departament de Mineralogia, Petrologia i Geologia Aplicada, Universitat de Barcelona, Martí Franquès s/n, Barcelona 08028, Spain
3
Unitat de Difracció de RX, Centres Científics i Tecnològics de la Universitat de Barcelona (CCiTUB), Solé i Sabarís 1-3, Barcelona 08028, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 13 May 2017 / Revised: 24 May 2017 / Accepted: 25 May 2017 / Published: 31 May 2017
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1189 KB, uploaded 1 June 2017]   |  

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through a modification of a previous synthetic sequence, in which the benzyloxymethyl hydroxyl protecting group has been replaced by methoxymethyl, to avoid the apparent formation of a benzyl ester derivative as a side product.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. View Full-Text
Keywords: polycycles; intramolecular cycloaddition; retrocycloaddition; domino reactions; X-ray diffraction polycycles; intramolecular cycloaddition; retrocycloaddition; domino reactions; X-ray diffraction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Camps, P.; Gómez, T.; Otermin, A.; Font-Bardia, M. Alternative Access to Functionalized 2,8-Ethanonoradamantane Derivatives. Molecules 2017, 22, 906.

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