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Singlet‐Oxygen‐Initiated Tandem Transformation of 2‐Hexylfuran to the Natural Alkaloids Glochidine and Glochidicine
Author(s) -
Ioannou Georgios I.,
Kalaitzakis Dimitris,
Vassilikogiannakis Georgios
Publication year - 2016
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.201600524
Subject(s) - chemistry , photooxygenation , singlet oxygen , photosensitizer , tandem , imidazole , combinatorial chemistry , stereochemistry , photochemistry , organic chemistry , oxygen , materials science , composite material
A synthesis of the imidazole alkaloids glochidine and glochidicine is presented. These natural products were prepared by the photooxygenation of a readily accessible alkylfuran precursor using histamine as a nitrogen source. By tailoring the choice of the photosensitizer as well as the conditions used for the cyclization of an N ‐acyliminium intermediate, the tandem reaction sequence could be manipulated to afford each of the natural products independently and as desired.