Alternative Access to Functionalized 2,8-Ethanonoradamantane Derivatives

作者：Camps Pelayo^*; Gomez Tania; Otermin Ane; Font Bardia Merce

来源：Molecules, 2017, 22(6): 906.

DOI：10.3390/molecules22060906

• polycycles
• intramolecular cycloaddition
• retrocycloaddition
• domino reactions
• X-ray diffraction

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through a modification of a previous synthetic sequence, in which the benzyloxymethyl hydroxyl protecting group has been replaced by methoxymethyl, to avoid the apparent formation of a benzyl ester derivative as a side product.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.

• 出版日期2017-6