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Mining the Tetraene Manifold: Total Synthesis of Complex Pyrones from Placobranchus ocellatus
Author(s) -
Miller Aubry K.,
Trauner Dirk
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.200500488
Subject(s) - polyene , natural product , isomerization , diastereomer , total synthesis , product (mathematics) , natural (archaeology) , cascade , chemistry , computer science , stereochemistry , content (measure theory) , information retrieval , mathematics , organic chemistry , history , archaeology , chromatography , geometry , catalysis , mathematical analysis
A natural product anticipated through total synthesis! Ocellapyrone A was obtained in the laboratory several months before the structure of this unusual natural product (see scheme) was reported. An isomerization/8π–6π electrocyclization cascade was used for the formation of the natural product from a polyene precursor. The synthesis of ocellapyrone B from a diastereomer of ocellapyrone A was also performed.
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