Total Synthesis of Two Possible Diastereomers of Natural 6‐Chlorotetrahydrofuran Acetogenin and Its Stereostructural Elucidation

The first total synthesis of two possible diastereomers of natural 6‐chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5‐exo‐tet cyclization, Z selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereosele...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-12, Vol.23 (68), p.17191-17194
Main Authors: Takamura, Hiroyoshi, Katsube, Tomoya, Okamoto, Kazuki, Kadota, Isao
Format: Article
Language:English
Subjects:
Absolute configuration
Acetogenins - chemical synthesis
Acetogenins - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Chemistry
Cyclization
Magnetic Resonance Spectroscopy
Molecular Conformation
natural products
Stereoisomerism
stereoselective synthesis
structure elucidation
Synthesis
tetrahydrofuran
total synthesis
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Summary:The first total synthesis of two possible diastereomers of natural 6‐chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5‐exo‐tet cyclization, Z selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereoselective chlorination. Comparison of their 1H and 13C NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (−)‐6‐chlorotetrahydrofuran acetogenin 1. True face: Stereoselective total synthesis of two possible diastereomers of natural 6‐chlorotetrahydrofuran acetogenin has been accomplished. The synthesis features 5‐exo‐tet cyclization, Z selective Wittig reaction and Julia olefination, and stereoinverted chlorination. Comparison of their NMR data and specific rotation with those of the natural product revealed the absolute configuration of natural (−)‐6‐chlorotetrahydrofuran acetogenin.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201703234