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Enantioselective Total Synthesis of the Polycyclic Guanidine‐Containing Marine Alkaloid (−)‐Batzelladine D
Author(s) -
Evans P. Andrew,
Qin Jun,
Robinson John E.,
Bazin Bérangère
Publication year - 2007
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.200700840
Subject(s) - enantioselective synthesis , azide , chemistry , total synthesis , iodide , guanidine , alkaloid , sequence (biology) , alkyl , stereochemistry , yield (engineering) , combinatorial chemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy
Addressing the marine core : The enantioselective total synthesis of the polycyclic guanidine‐containing marine alkaloid (−)‐batzelladine D has been accomplished using a convergent 14‐step reaction sequence (longest linear sequence) in 10 % overall yield. The ability to accomplish the selective homolytic cleavage of an alkyl iodide in the presence of an azide circumvents the necessity for nitrogen‐protecting groups.