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A Photoinduced Cyclization Cascade—Total Synthesis of (−)‐Leuconoxine
Author(s) -
Pfaffenbach Magnus,
Gaich Tanja
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500656
Subject(s) - total synthesis , domino , enantioselective synthesis , cascade , indole alkaloid , chemistry , stereochemistry , radical cyclization , indole test , cascade reaction , organic chemistry , catalysis , chromatography
A protecting‐group‐free and enantioselective total synthesis of the monoterpenoid indole alkaloid (−)‐leuconoxine was accomplished. The key step comprises a novel photoinduced domino macrocyclization/transannular cyclization involving the Witkop cyclization, for which additional mechanistic evidence is provided. This process furnishes a diaza[5.5.6.6]fenestrane skeleton, which is a hitherto unprecedented structure element.