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Synthesis of rac ‐Midpacamide and the spiro ‐Cyclization of Its Precursor
Author(s) -
Lindel Thomas,
Hoffmann Holger
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970731
Subject(s) - chemistry , moiety , pyrrole , hydantoin , acetic acid , natural product , bromine , ring (chemistry) , ruthenium , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry
The alkylidene hydantoin 8 was synthesized as an analogue of the marine natural product oroidin ( 1 ) by employing a Horner‐Wadsworth‐Emmons reaction. Treatment of 8 with bromine in acetic acid induced a biomimetic spiro ‐cyclization forming the ACD ring system of dibromophakellin ( 2 ) in one step. rac ‐Midpacamide ( 10 ) was obtained from the same precursor through a chemoselective, ruthenium‐catalyzed hydrogenation leaving the brominated pyrrole moiety intact.