1978
DOI: 10.1021/ar50126a003
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Phosphorylation by means of cyclic enediol phosphates

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1978
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Cited by 18 publications
(2 citation statements)
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“…Comparison of the relative polarities and C-15 proton chemical shifts of these products with those reported106 for 4-dehydrobrefeldin-A 7-methoxymethyl ether (7?/0.40, 4.68) and its C-15 epimer (7?y0.45, 5.23) allowed a tentative (correct) C-15 stereochemical assignment to be made. Thus, the more polar -oxocrotonate 24b was treated with sodium borohydride in methanol at -78 °C to give alcohol 24c as a unique, highly crystalline product in 85-95% yield 48 Following silylation of the C-4 hydroxyl, conveniently effected with (trimethylsilyl)diethylamine,49 the C-7 methyl ether was cleaved by using chlorotrimethylsilane and anhydrous sodium iodide in dry acetonitrile50 under very precisely controlled conditions to afford crystalline racemic brefeldin-A (1) in approximately 60% yield. This material was indistinguishable spectroscopically (IR, NMR, MS) and chromatographically (TLC, HPLC) from the natural product.…”
Section: Scheme IIImentioning
confidence: 99%
See 1 more Smart Citation
“…Comparison of the relative polarities and C-15 proton chemical shifts of these products with those reported106 for 4-dehydrobrefeldin-A 7-methoxymethyl ether (7?/0.40, 4.68) and its C-15 epimer (7?y0.45, 5.23) allowed a tentative (correct) C-15 stereochemical assignment to be made. Thus, the more polar -oxocrotonate 24b was treated with sodium borohydride in methanol at -78 °C to give alcohol 24c as a unique, highly crystalline product in 85-95% yield 48 Following silylation of the C-4 hydroxyl, conveniently effected with (trimethylsilyl)diethylamine,49 the C-7 methyl ether was cleaved by using chlorotrimethylsilane and anhydrous sodium iodide in dry acetonitrile50 under very precisely controlled conditions to afford crystalline racemic brefeldin-A (1) in approximately 60% yield. This material was indistinguishable spectroscopically (IR, NMR, MS) and chromatographically (TLC, HPLC) from the natural product.…”
Section: Scheme IIImentioning
confidence: 99%
“…1971, 93, 2677. See also: (1) Berson, J. A.; Walia, J. S.; Remanick, A.; Suzuki, S.; Reynolds-Warnhoff, P.; Willner, D. Ibid.…”
mentioning
confidence: 99%