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|a Toward a formal synthesis of Laureatin: unexpected rearrangements involving cyclic ether nucleophiles |h [electronic resource]. |
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|a Washington, DC : |b American Chemical Society, |c 2012. |
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|a pages 7883-7890 : |b illustrations (some color). |
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|a Published IN: Journal of organic chemistry, Vol. 77 (2012 August). |
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|a Laureatin, a metabolite of the red algae Laurencia nipponica, has shown potent activity as a mosquito larvicide. The two previously published syntheses of laureatin involved an initial preparation of the 8-membered cyclic ether, followed by formation of the oxetane ring. Our strategy was the reverse, i.e., to utilize an oxetane as the framework to construct the larger ring. During this work, attempted N-bromosuccinimide (NBS)-mediated cyclization of oxetane alcohol 17, prepared from readily accessible 2-methyleneoxetane 12, yielded epoxytetrahydrofuran 19rather than the expected laureatin core. Further derivatization of 19 yielded transfused bis-tetrahydrofuran 32. The synthesis of 19 and 32, as well as structural and stereochemical elucidation studies, are described. |
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|a Electronic reproduction. |c University of the Virgin Islands, |d 2016. |f (UVI Digital Library) |n Mode of access: World Wide Web. |n System requirements: Internet connectivity; Web browser software. |
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|a University of the Virgin Islands. |
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|a Castillo, Bernard F., II. |
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|a UVI |c Faculty Publications |
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|u https://uvi.sobeklibrary.com/AA00000019/00001 |y Click here for full text |
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|a https:/uvi.sobeklibrary.com/content/AA/00/00/00/19/00001/jo301048zthm.jpg |
