细胞毒性产乙酸素吡喃霉素的全合成

Total synthesis of a cytotoxic acetogenin, pyranicin.

作者信息

Takahashi Shunya, Kubota Akemi, Nakata Tadashi

机构信息

RIKEN-The Institute of Physical and Chemical Research, Wako, Saitama 351-0198, Japan.

出版信息

Org Lett. 2003 Apr 17;5(8):1353-6. doi: 10.1021/ol034323m.

DOI:10.1021/ol034323m

PMID:12688757

Abstract

[structure: see text] The first total synthesis of a new cytotoxic acetogenin, pyranicin (1), is described. SmI(2)-induced reductive cyclization of beta-alkoxy acrylate 4 proceeded stereoselectively to give 16,20-syn-19,20-trans-THP derivative 14, which was efficiently transformed into the 19,20-cis-THP derivative 18 through Mitsunobu lactonization. Wittig reaction of the phosphonium salt 2 obtained therefrom with butenolide 3 at -78 degrees C followed by reduction and deprotection afforded 1 in good overall yield.

摘要

[结构：见正文] 描述了一种新的细胞毒性产乙酸素——吡喃霉素（1）的首次全合成。二碘化钐诱导的β-烷氧基丙烯酸酯4的还原环化反应立体选择性地进行，得到16,20-顺式-19,20-反式-四氢吡喃衍生物14，通过光延内酯化反应将其有效地转化为19,20-顺式-四氢吡喃衍生物18。由此得到的鏻盐2与丁烯内酯3在-78℃下进行维蒂希反应，随后进行还原和脱保护，以良好的总收率得到1。