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

Hiroyoshi Takamura; Tomoya Katsube; Kazuki Okamoto; Isao Kadota

doi:10.1002/chem.201703234

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

Hiroyoshi Takamura, Tomoya Katsube, Kazuki Okamoto, Isao Kadota

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	17191-17194
Number of pages	4
Journal	Chemistry - A European Journal
Volume	23
Issue number	68
DOIs	https://doi.org/10.1002/chem.201703234
Publication status	Published - Dec 6 2017

Keywords

natural products
stereoselective synthesis
structure elucidation
tetrahydrofuran
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "Total Synthesis of Two Possible Diastereomers of Natural 6-Chlorotetrahydrofuran Acetogenin and Its Stereostructural Elucidation",

abstract = "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.",

keywords = "natural products, stereoselective synthesis, structure elucidation, tetrahydrofuran, total synthesis",

author = "Hiroyoshi Takamura and Tomoya Katsube and Kazuki Okamoto and Isao Kadota",

note = "Funding Information: We thank Professor Vassilios Roussis (University of Athens) for valuable discussion on the NMR data of natural 6-chlorotetrahydrofuran acetogenin 1. This work was supported by JSPS KA-KENHI Grant Number 17K05862. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/chem.201703234",

language = "English",

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AU - Takamura, Hiroyoshi

AU - Katsube, Tomoya

AU - Okamoto, Kazuki

AU - Kadota, Isao

N1 - Funding Information: We thank Professor Vassilios Roussis (University of Athens) for valuable discussion on the NMR data of natural 6-chlorotetrahydrofuran acetogenin 1. This work was supported by JSPS KA-KENHI Grant Number 17K05862. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/12/6

Y1 - 2017/12/6

N2 - 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.

AB - 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.

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KW - stereoselective synthesis

KW - structure elucidation

KW - tetrahydrofuran

KW - total synthesis

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

Abstract

Keywords

ASJC Scopus subject areas

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