Barriault Louis, Ang Patrick J A, Lavigne Roch M A
Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5.
Org Lett. 2004 Apr 15;6(8):1317-9. doi: 10.1021/ol049680r.
The first synthesis of the tricyclic core of Penostatin F (1) using a stereocontrolled Diels-Alder reaction and a Claisen rearrangement in succession has been achieved in nine steps from commercially available methyl acetoacetate and (E)-2-decenal. Penostatin F is a metabolite isolated from a fungal strain of Penicillium sp., OUPS-79, separated from the marine alga Enteromorphia intestinalis and exhibits significant cytotoxicity against cultured P388 Leukemia cells (ED(50) = 1.4 micromol/mL). [reaction: see text]
首次通过立体控制的狄尔斯-阿尔德反应和克莱森重排相继实现了从市售的乙酰乙酸甲酯和（E）-2-癸烯醛出发，经九步合成了Penostatin F（1）的三环核心。Penostatin F是从青霉菌属的真菌菌株OUPS-79中分离得到的一种代谢产物，该菌株从海洋藻类肠浒苔中分离出来，对培养的P388白血病细胞具有显著的细胞毒性（ED(50) = 1.4微摩尔/毫升）。[反应：见正文]
