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Sceptrin as a Potential Biosynthetic Precursor to Complex Pyrrole–Imidazole Alkaloids: The Total Synthesis of Ageliferin
Author(s) -
Baran Phil S.,
O'Malley Daniel P.,
Zografos Alexandros L.
Publication year - 2004
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.200453937
Subject(s) - pyrrole , imidazole , total synthesis , chemistry , alkaloid , magic (telescope) , stereochemistry , combinatorial chemistry , organic chemistry , physics , quantum mechanics
Microwave‐induced magic : There is a widely held conviction that the antiviral marine alkaloid ageliferin 1 arises biosynthetically from a Diels–Alder reaction which, although possible, has yet to materialize in the laboratory. A total synthesis of 1 from sceptrin is now reported that has led to a new hypothesis for how 1 and other dimeric pyrrole‐imidazole alkaloids might be formed in nature.