Total Synthesis of the Marine Natural Product  rac ‐Dibromophakellstatin | Zendy

Jacquot Delphine E. N. | Zendy; Zöllinger Michael | Zendy; Lindel Thomas | Zendy

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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.

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