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Total Synthesis and Determination of the Absolute Configuration of (−)‐Dolabriferol
Author(s) -
Laclef Sylvain,
Turks Maris,
Vogel Pierre
Publication year - 2010
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.201003735
Subject(s) - absolute (philosophy) , total synthesis , enol , silylation , absolute configuration , trimethylsilyl , cascade , computer science , natural product , product (mathematics) , chemistry , stereochemistry , organic chemistry , philosophy , mathematics , epistemology , chromatography , catalysis , geometry
A reaction cascade combining sulfur dioxide with a 1‐oxy‐1,3‐diene and ( E )‐silyl enol ether formed the basis of a short total synthesis of (−)‐dolabriferol (see scheme; TMS=trimethylsilyl). The absolute configuration of this natural product, which was first extracted from a gastropod mollusc in 1996, was established unequivocally.