Total Synthesis of (±)-Terpestacin and (±)-11-epi-Terpestacin

The total synthesis of racemic terpestacin and 11-epi-terpestacin using the allene ether Nazarov reaction as the key step is described. All stereochemistry is derived from the stereogenic carbon atom that is formed during the Nazarov reaction.

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Bibliographic Details
Published in:Journal of organic chemistry 2007-08, Vol.72 (17), p.6473-6480
Main Authors: Berger, Gideon O, Tius, Marcus A
Format: Article
Language:English
Subjects:
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Chemistry
Exact sciences and technology
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Stereoisomerism
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Description
Summary:The total synthesis of racemic terpestacin and 11-epi-terpestacin using the allene ether Nazarov reaction as the key step is described. All stereochemistry is derived from the stereogenic carbon atom that is formed during the Nazarov reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070923d