Total Synthesis and Determination of the Absolute Configuration of (−)‐Dolabriferol | Zendy

Laclef Sylvain | Zendy; Turks Maris | Zendy; Vogel Pierre | Zendy

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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.

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