The Stille coupling reaction of 3-(benzyloxymethyl)-1-(tert-butyldiphenylsiloxy)ethyl-1-(tributylstannyl)allene with N-(tert-butoxycarbonyl)-2-iodoaniline directly produced the corresponding 2-vinylindole derivative, which was independently transformed into natural (-)-goniomitine and unnatural (+)-goniomitine via the cross-metathesis with chiral oxazolopiperidone lactams. The antiproliferative activity of the synthesized natural (-)-goniomitine in Mock and MDCK/MDR1 cells showed them to be more potent to retard cell growth than unnatural (+)-goniomitine.
Total synthesis of (+)-kopsihainanine A was accomplished on the basis of (i) Stoltz's enantioselective decarboxylative asymmetric allylation and (ii) the proposed biogenetic pathway from the related alkaloid, kopsihainanine B. In addition, HPLC analysis of the synthetic (+)-kopsihainanine A confirmed its ee to be 99% with [α] = 25.35.
The two conditions for the preparation of the reactive N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane intermediate were developed by the reaction of the N-(tert-butoxycarbonyl)-2-(1-ethoxycarbonyloxymethylallenyl)aniline with K(2)CO(3) or Pd(2)(dba)(3) in refluxing toluene. The resulting N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane was captured by several alkenyl and alkynyl dienophiles to provide the corresponding tetrahydro- and dihydrocarbazole derivatives.
(7), and [Cu(5) 2 ] (8) with bis(pentafluorobenzoyl)methane (H5) and to understand the fluorine-substituted effects. While the coordination mode of the partially fluorinated complexes was quite similar to the fully fluorinated complexes, the intra-and intermolecular π-interactions of the ligand moieties were highly influenced by the fluorination effects; the arene-perfluoroarene interactions were observed in complexes 2 and 3 as a reason of the dinucleation. In this paper, we describe detail structures of the protonated form of the ligand, H1, and complexes 2-4 by X-ray crystallographic studies.
The title complex comprises two Ni(2+) ions, four fluorinated ligands and two water molecules in a centrosymmetric dinuclear complex. This compound was crystallized from benzene-CH(2)Cl(2), and two types of crystals, viz. the title benzene tetrasolvate, [Ni(2)(C(15)HF(10)O(2))(4)(H(2)O)(2)].4C(6)H(6), (I), and the previously reported benzene disolvate, [Ni(2)(C(15)HF(10)O(2))(4)(H(2)O)(2)].2C(6)H(6), (II) [Hori et al. (2009). Bull. Chem. Soc. Jpn, 82, 96-98], were obtained as pseudopolymorphs. In the crystal structure of (I), the four benzene solvent molecules interact closely with all the pentafluorophenyl groups of the complex through arene-perfluoroarene interactions. The molecular structures of the two compounds show essentially the same conformation, although the benzene molecules are accommodated in a columnar packing in (I), while they are isolated from each other in (II).
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