Enantioselective syntheses of isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin
Enantioselective syntheses of isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin
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DOI：
10.1021/ol000179i
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发表时间：
2000-09-21
期刊：
影响因子：
5.2
通讯作者：
O'Doherty, GA
中科院分区：
文献类型：
--
作者：
Harris, JM;O'Doherty, GA
GRAPHICSA灵活的高度官能化的α，β-不饱和δ-内酯的对映选择性路线允许从糠醛分别以10%、5%和13%的总产率合成苯乙烯基内酯：异α-内酯、3-表α-内酯和5-羟基角柳胺。该方法通过将Sharpless催化不对称二羟基化作用应用于乙烯基呋喃来获得其不对称性。所得二醇以高对映体过量产生，并且可以经由短的高度非对映选择性氧化和还原序列立体选择性地转化为α，β-不饱和δ-内酯。
GRAPHICSA flexible enantioselective route to highly functionalized alpha,beta-unsaturated delta-lactones has allowed for the syntheses of the styryllactones: isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin in 10%, 5%, and 13% overall yields from furfural, respectively. This approach derives its asymmetry by applying the Sharpless catalytic asymmetric dihydroxylation to vinylfuran. The resulting diols are produced in high enantioexcess and can be stereoselectively transformed into alpha,beta-unsaturated delta-lactones via a short highly diastereoselective oxidation and reduction sequence.