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Total Synthesis of the Marine Natural Product rac ‐Dibromophakellstatin
Author(s) -
Jacquot Delphine E. N.,
Zöllinger Michael,
Lindel Thomas
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200462252
Subject(s) - annulation , pyrrole , natural product , total synthesis , samarium , chemistry , stereochemistry , imidazole , key (lock) , ring (chemistry) , combinatorial chemistry , computer science , organic chemistry , catalysis , computer security
The pyrrole‐imidazole alkaloid dibromophakellstatin ( 1 ) from the marine sponge Phakellia mauritiana was synthesized in only five steps starting from L ‐prolinol. The key step of the synthesis is the direct annulation of the imidazolinone ring to a pyrrolopyrazinone precursor by employing an ethoxycarbonylnitrene generated in situ. Samarium diiodide proved to be the best choice for the chemoselective, stepwise deprotection of the resulting tetracycle. Ts=toluenesulfonyl.