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Highly Functionalized, Angularly Anellated Aromatic Compounds from Dendralenes
Author(s) -
Hopf Henning,
Yildizhan Şeref
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001536
Subject(s) - chemistry , aromatization , anthracene , phenanthrene , dimethyl acetylenedicarboxylate , diene , organic chemistry , medicinal chemistry , stereochemistry , cycloaddition , catalysis , natural rubber
[3]Dendralene ( 2 ) has been converted into the benz[ a ]anthracene tetraester 13 in a protocol involving diene‐transmissive Diels–Alder addition of dimethyl acetylenedicarboxylate to 2 followed by a sequence of reduction–addition–aromatization reactions. Likewise, the next higher vinylog [4]dendralene ( 19 ) provided the phenanthrene hexaester 21 . An attempt to prepare the double o ‐xylylene intermediate 17 failed.