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Chemistry. 2017 Dec 6;23(68):17191-17194. doi: 10.1002/chem.201703234. Epub 2017 Nov 22.

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

Author information

1
Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.

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 1 H and 13 C 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

PMID:
29083058
DOI:
10.1002/chem.201703234
[Indexed for MEDLINE]
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