scholarly journals Stereoselective Convergent Synthesis of Carbon Skeleton of Cotylenin A Aglycone

Synthesis ◽  
2021 ◽  
Author(s):  
Kazuyuki Sugita ◽  
Motoi Kuwabara ◽  
Ami Matsuo ◽  
Shogo Kamo ◽  
Akinobu Matsuzawa

AbstractIn this paper, the synthesis of the carbon skeleton of cotylenin A aglycone is described. The key reactions, including an intramolecular aldol reaction, an aldol coupling reaction, and a ring-closing meta­thesis, allow for the effective and stereoselective access to the carbon skeleton of cotylenin A aglycone. The stereochemistry was confirmed by single-crystal X-ray crystallographic analyses of related compounds.

2004 ◽  
Vol 57 (7) ◽  
pp. 689 ◽  
Author(s):  
Zhi-Long Chen ◽  
Ronald N. Warrener ◽  
Douglas N. Butler

1,2-Bis(2,2′:6′,2′′-terpyridin-4′yl)ethanone 7, an unsymmetrically linked bis-tridentatate ligand, was prepared by treatment of 4′-cyanomethylterpyridine 10 (RT, overnight) or 4′-(methoxycarbonylmethyl)terpyridine 11 (60°C, 7 h) with concentrated hydrochloric acid. These conversions, which involved an unprecedented homo-coupling reaction, are discussed with the structure of 7 being confirmed by X-ray single crystal analysis. The nitrile starting material 10 was prepared by reaction of the mesylate 9, derived from the known 4′-hydroxymethylterpyridine 8 with sodium cyanide, while ester 11 was prepared by reaction of 10 with methanol in the presence of concentrated sulfuric acid.


2016 ◽  
Vol 120 (39) ◽  
pp. 7778-7785 ◽  
Author(s):  
Ayelén Florencia Crespi ◽  
Daniel Vega ◽  
Ana Karina Chattah ◽  
Gustavo Alberto Monti ◽  
Graciela Yolanda Buldain ◽  
...  

2018 ◽  
Vol 73 (8) ◽  
pp. 583-587
Author(s):  
Mustafa M. El-Abadelah ◽  
Firas F. Awwadi ◽  
Hamdallah A. Hodali ◽  
Rasha S. Rawajfeh ◽  
Monther S. Zreid ◽  
...  

AbstractDichloro[3-(pyridin-2-yl)-1,2,4-triazinone]Pd(II) undergoes oxidative C–C coupling reaction with cyclopentanone and cyclohexanone at 110°C to yield the respective Pd complexes, chloro[1-(4-chlorophenyl)-5-(2-hydroxycyclopent-1-enyl)-3-(pyridin-2-yl)-1,2,4-triazin-6(1H)-one]palladium(II) (3) and chloro[1-(4-chlorophenyl)-5-(2-hydroxycyclohex-1-enyl)-3-(pyridin-2-yl)-1,2,4-triazin-6(1H)-one]palladium(II) (4). The structures of both complexes are supported by spectral data and confirmed by single-crystal X-ray crystallography. The molecules 3 and 4 stack to form tunnel structures, whilst the geometry around the palladium ion is square planar.


2008 ◽  
Vol 61 (7) ◽  
pp. 506 ◽  
Author(s):  
Magne O. Sydnes ◽  
Anna Bezos ◽  
Christopher Burns ◽  
Irma Kruszelnicki ◽  
Christopher R. Parish ◽  
...  

A series of enantiomerically pure C8c–C15 monoseco analogues, 23–30, of the alkaloids cryptopleurine (1) and julandine (2) have been prepared using cinnamyl chloride 37 and (S)- or (R)-2-methylpiperidine as key building blocks. Two related compounds, 31 and 32, have also been synthesized. Each of these analogues has been subjected to various biological evaluations and most of them show dramatically reduced cytotoxicity compared with parent system 1. Nevertheless, they are potent anti-angiogenic agents. The formation and single-crystal X-ray analysis of the spirocyclic dienone 54, a by-product arising from attempts to prepare analogue 32, is also described.


Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 862 ◽  
Author(s):  
Angelika Lásiková ◽  
Jana Doháňošová ◽  
Mária Štiblariková ◽  
Martin Parák ◽  
Ján Moncol ◽  
...  

The paper describes the first total synthesis of natural varioxiranol A by chiral pool approach and confirmation of its absolute configuration by single-crystal X-ray analysis. The target varioxiranol A and its 4-epimer were obtained after 10 steps from single and available chiral source 1,2-O-isopropylidene-d-glyceraldehyde in an overall yield of 10% and 6%, respectively. A synthetic strategy based on the Julia–Kocieński coupling reaction between aromatic sulfone and corresponding aldose derivative makes it possible to prepare other interesting polyketide derivatives (varioxiranols B-G, varioxirane, varioxiranediols).


2017 ◽  
Vol 72 (7) ◽  
pp. 517-521
Author(s):  
Olaf Reckeweg ◽  
Armin Schulz ◽  
Francis J. DiSalvo

AbstractThe crystal structure of NH4[C(CN)3] has been determined via X-ray single-crystal methods at 203(2) K corroborating earlier results. Additionally, the hydrogen positions have been determined and the Raman spectrum of the title compound recorded on single crystals. The spectroscopic results are compared to those for related compounds.


Author(s):  
Jianxin Song ◽  
Yan Fan ◽  
Zhiming Zeng ◽  
Hui Shu ◽  
Mingbo Zhou ◽  
...  

A powerful and concise synthesis of two- and three-dimensional β,β’-N-heterocycle fused porphyrins by palladium-catalyzed C-N coupling reaction of bromoporphyrins with arylamines has been demonstrated. Single crystal X-ray crystallographic analysis revealed...


1996 ◽  
Vol 51 (6) ◽  
pp. 826-831 ◽  
Author(s):  
Stefan Peschel ◽  
Werner Paulus ◽  
Dietrich Babel

Abstract The crystal structures of four isotypic cyano complexes, belonging to the monoclinic type of cryolite (P21/n, Z = 2), were determined by single crystal X-ray methods and in one case also by neutron diffraction: Rb2LiFe(CN)6 (a = 717.3, b = 748.0, c = 1030.2 pm, β = 90.24°; Fe - C = 193.6, C - N = 114.5, Li - N = 227.0 pm), Rb,NaFe(CN)6 (a = 724.5, b = 772.5, c = 1055.2 pm, β = 90.39°; Fe - C = 193.9, C - N = 114.2, Na - N = 250.4 pm), Rb,LiCo(CN)6 (a = 715.5, b = 741.2, c = 1025.0 pm, β = 90.14°; Co - C = 189.6, C - N = 114.3, Li - N = 226.9 pm), Rb2NaCo(CN)6 (a = 722.5, b = 766.3, c = 1049.2 pm, β = 90.33°; Co - C = 189.9 (188.8), C - N = 113.4 (7/5.5), Na - N = 250.6 (249.6 pm). The irregular [RbN8l coordination polyhedra exhibit average distances close to Rb - N = 336 pm. Details are discussed and the results compared with those of related compounds


1994 ◽  
Vol 49 (5) ◽  
pp. 581-584 ◽  
Author(s):  
G. Tams ◽  
Hk. Müller-Buschbaum

Single crystals of Sr3.67Na0.33PtO6 were prepared by heating oxide mixtures in closed silver tubes and investigated by X-ray single crystal techniques. It crystallizes with trigonal symme­try, space group D63d-R3̅c (Nr. 167) with a = 9.6617, c = 11.6580 Å, Z = 6. Sr3.67Na0.33PtO6 belongs to the Sr4PtO6 type and is isotypic to K4CdCl6. One point position characterized by a trigonal prismatic O2- coordination is occupied by Na+ and Sr2+ statistically. The crystal structure is discussed with respect to the related compounds Sr3CuPtO6 and Ca3. 5Cu0.5PtO6.


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