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Total Synthesis of (+)‐Dibromophakellin
Author(s) -
Imaoka Takuya,
Iwamoto Osamu,
Noguchi Keiichi,
Nagasawa Kazuo
Publication year - 2009
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.200806233
Subject(s) - aminal , congener , pyrrole , imidazole , stereochemistry , enantiomer , chemistry , organic chemistry
Two members of a family of pyrrole–imidazole marine alkaloids, (+)‐dibromophakellin and the nonnatural congener (+)‐phakellin, were synthesized enantioselectively from 4‐hydroxy‐ L ‐proline. The chiral aminal at C10 was constructed efficiently by means of an Overman‐type [3,3] sigmatropic rearrangement of an enamide (see scheme).