Integral Stereocontrolled Synthesis of a Spiro-norlignan, Sequosempervirin A: Revision of Absolute Configuration

A novel synthetic path to sequosempervirin A was established by employing a samarium diiodide promoted intramolecular Barbier-type reaction of the lactonic iodide, in which the key structural feature, a spiro[4.5]decane ring system, could be constructed by controlling the stereochemistry of the hydr...

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Bibliographic Details
Published in:Organic letters 2011-09, Vol.13 (17), p.4640-4643
Main Authors: Ito, Yuji, Takahashi, Kazunori, Nagase, Hiromasa, Honda, Toshio
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary:A novel synthetic path to sequosempervirin A was established by employing a samarium diiodide promoted intramolecular Barbier-type reaction of the lactonic iodide, in which the key structural feature, a spiro[4.5]decane ring system, could be constructed by controlling the stereochemistry of the hydroxyl group at the 8-position. The absolute configuration of natural sequosempervirin A was revised to be 4S based on this synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2018533