期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 19, 页码 7616-7624出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo801338t
关键词
-
资金
- Engineering and Physical Sciences Research Council
- University of Birmingham
Two trisubstituted epimeric tetrahydrofurans, 1 and 2, have been synthesized in order to confirm the relative stereochemistry in the natural product aureonitol. The key step in the synthesis of 1 and 2 involved a stereoselective intramolecular allylation of an allylsilane with an aldehyde, which introduced the stereotriad in the five-membered ring. The major tetrahydrofuran diastereoisomer 18 from this cyclization reaction was subsequently elaborated to tetrallydrofuran 1. Its 3-epimer (2) was then prepared from 1 via an oxidation - reduction sequence. Compound 1 exhibits identical (1)H NMR data to those reported for aureonitol, which was isolated from Helichrysum aureonitons by Bohlmann in 1979, whereas the (1)H NMR data for 2 are markedly different. The (1)H NMR data (in CDCl(3), CD(3)OD, and C(6)D(6)) and (13)C NMR data (in CDCl(3)) for 1 are also identical with those reported for a natural product isolated from various Chaetomiun sp. by Abraham. Seto, and Teuscher. These findings support Abraham's conclusion that the structure of aureonitol should be revised from 2 to 1. The enantioselective synthesis of 1 has also confirmed that (-)-aureonitol isolated by Abraham contains the (2S,3R,4S) absolute configuration of stereocenters on the tetrahydrofuran ring.
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