Lee Taeho, Lee Sukjin, Kwak Young Shin, Kim Deukjoon, Kim Sanghee
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea.
Org Lett. 2007 Feb 1;9(3):429-32. doi: 10.1021/ol062756u.
[reaction: see text] The syntheses of the cytotoxic natural product pachastrissamine and its unnatural 4-epi-congener were accomplished starting from a natural phytosphingosine. The relatively unstrained cyclic sulfate intermediate smoothly underwent the 5-endo cyclization to yield the 2,3,4-trisubstituted tetrahydrofuran ring system of pachastrissamine. The corresponding epoxy alcohol afforded the 4-epi-congener via a tosylate-mediated double inversion process.
[反应：见正文] 细胞毒性天然产物帕卡司他明及其非天然4-表-类似物的合成是从一种天然植物鞘氨醇开始完成的。相对无张力的环状硫酸酯中间体顺利地进行了5-内型环化反应，生成了帕卡司他明的2,3,4-三取代四氢呋喃环系。相应的环氧醇通过对甲苯磺酸酯介导的双反转过程得到4-表-类似物。
