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A Concise Total Synthesis of (±)‐Vigulariol
Author(s) -
Clark J. Stephen,
Hayes Stewart T.,
Wilson Claire,
Gobbi Luca
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.200603880
Subject(s) - key (lock) , yield (engineering) , computer science , content (measure theory) , information retrieval , world wide web , mathematics , computer security , physics , mathematical analysis , thermodynamics
From the deep : Vigulariol has been efficiently synthesized in 20 steps and 4.0 % overall yield from commercially available starting materials. Key to the synthesis was the use of copper(II) hexafluoroacetylacetate [Cu(hfacac) 2 ] to form the oxabicyclo[6.2.1]undecene system (see scheme; TBS= tert ‐butyldimethylsilyl). The strategy should provide access to other members of the cladiellin family.