Kapferer Tobias, Brückner Reinhard, Herzig Axel, König Wilfried A
Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität, Albertstrasse 21, 79104 Freiburg, Germany.
Chemistry. 2005 Mar 18;11(7):2154-62. doi: 10.1002/chem.200401135.
Both enantiomers of the gamma-chiral alpha,beta-dimethylated butyrolactones nat-1 and nat-2 from the moss Plagiomnium undulatum were synthesized stereoselectively through butenolides and tetronic acids, respectively. The configuration of the natural products was determined by GLC comparisons with mono(3-O-acetyl-6-O-tert-butyldimethylsilyl-2-O-methyl)hexakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-beta-cyclodextrin as a stationary phase.
分别通过丁烯内酯和特窗酸，立体选择性地合成了来自波叶仙鹤藓的γ-手性α,β-二甲基丁内酯nat-1和nat-2的两种对映体。天然产物的构型通过使用单(3-O-乙酰基-6-O-叔丁基二甲基甲硅烷基-2-O-甲基)六(6-O-叔丁基二甲基甲硅烷基-2,3-二-O-甲基)-β-环糊精作为固定相的气相色谱比较来确定。
