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Synthesis of a vinylchlorine-containing 1,3-diol from a marine cyanophyte
Alternative Title由海洋蓝藻分离得到的含有烯基氯的1,3-二醇的合成
Wang XL(王晓龙)1; Yang YY(杨洋洋)1; Chen HJ(陈慧君)1; Wu YK(伍贻康)1; Ma DS(马东升)1
Source PublicationTetrahedron
AbstractUsing epoxy chiral building blocks readily derived from D-gluconolactone as the source of the stereogenic centers, both (6R,8R)- and (6R,8S)-isomers of (E)-1-chlorotridec-1-ene-6,8-diol were synthesized. The vinylchloro unit was installed onto the substrate carbon chain in an approximately 9:1 (E)/(Z) ratio via a condensation of CrCl2/CHCl3 with a terminal aldehyde. A tosylation protocol featuring addition of H2O was also developed for a highly polar tetraol. The synthetic products allowed for re-acquisition of the NMR spectra of better quality and revealed some delicate yet unignorable discrepancies in the C-13 NMR for the natural isomer obtained by synthesis and that isolated some 30 years ago from the marine cyanophyte. The puzzling discrepancies were eventually shown to be caused by deuteration of the hydroxyl groups. (C) 2014 Elsevier Ltd. All rights reserved.
Subject Area生命有机化学
Indexed BySCI
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Document Type期刊论文
Corresponding AuthorWu YK(伍贻康); Ma DS(马东升)
Recommended Citation
GB/T 7714
Wang XL,Yang YY,Chen HJ,et al. Synthesis of a vinylchlorine-containing 1,3-diol from a marine cyanophyte[J]. Tetrahedron,2014,70(30):4571-4579.
APA 王晓龙,杨洋洋,陈慧君,伍贻康,&马东升.(2014).Synthesis of a vinylchlorine-containing 1,3-diol from a marine cyanophyte.Tetrahedron,70(30),4571-4579.
MLA 王晓龙,et al."Synthesis of a vinylchlorine-containing 1,3-diol from a marine cyanophyte".Tetrahedron 70.30(2014):4571-4579.
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