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Enantioselective Synthesis of (+)‐Monobromophakellin and (+)‐Phakellin: A Concise Phakellin Annulation Strategy Applicable to Palau'amine
Author(s) -
Wang Shaohui,
Romo Daniel
Publication year - 2008
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.200703998
Subject(s) - enantioselective synthesis , annulation , aminal , guanidine , amine gas treating , stereochemistry , chemistry , combinatorial chemistry , organic chemistry , catalysis
A unique oxidative cyclization of a tricycle bearing a guanidine aminal provides a concise route to the enantioselective synthesis of (+)‐phakellin and (+)‐monobromophakellin in nine and ten steps, respectively, starting from L ‐proline (see scheme). This sequence provides a simple annulation strategy applicable to the preparation of more complex members of this family of marine sponge‐derived alkaloids including palau'amine.