scholarly journals Stereoselective preparation of mono- and bis-derivatives of pentacyclo[6.3.0.02,6.03,10.05,9] undecane (D 3-trishomocubane)

2013 ◽  
Vol 11 (12) ◽  
pp. 2144-2150 ◽  
Author(s):  
Anastasiia Mishura ◽  
Anna Sklyarova ◽  
Dmitriy Sharapa ◽  
Igor’ Levandovsky ◽  
Michael Serafin ◽  
...  

AbstractThe rearrangement of easily accessible Cookson’s diketone with chlorosulfonic acid in chloroform followed by the acidic hydrolysis gave 6-chloro-7-hydroxy-dichloropentacyclo[6.3.0.02,6.03,10.05,9]undecane-4-one, whose syn-stereochemistry was assigned through the X-ray crystal structure analysis. This key structure was used for the stereoselective synthesis of the D 3-trishomocubane derivatives as well as for the preparation of potential drugs bearing hydroxy- and amino-functional groups. A new multigram preparative synthesis of D 3-trishomocubane was developed.

1983 ◽  
Vol 61 (2) ◽  
pp. 282-283 ◽  
Author(s):  
Stanley C. Nyburg ◽  
Pik Y. Siew ◽  
Gavin N. Saunders ◽  
John R. Purdy ◽  
Stewart McLean

The structure and absolute configuration of a bisepoxide (2) produced by oxidation of tetraacetylsecologanin dimethyl acetal (1) with m-chloroperbenzoic acid have been established by X-ray crystal structure analysis. Epoxidation of the vinyl side chain is unexceptional; epoxidation of the β-alkoxyacrylate moiety is novel. This determination represents a valuable bench mark for configurational assignments, since the bisepoxide has been correlated by chemical transformations with a number of synthetic and naturally-occurring derivatives of secologanin.


Synlett ◽  
2021 ◽  
Author(s):  
Hong-Wu Zhao ◽  
Xiao-Fan Bi ◽  
Hai-Liang Pang ◽  
Zhe Tang ◽  
Heng Zhang ◽  
...  

In the presence of Na2CO3, the conjugate addition between α-halogeno hydrazones and nitroso compounds proceeded readily, thus delivering multifunctionalized nitrones in the reasonable chemical yields with excellent strereoselectivities. The chemical structure and stereochemical configuration of title chemical entities were unambiguously identified by an X-ray single crystal structure analysis.


Synthesis ◽  
2020 ◽  
Vol 52 (23) ◽  
pp. 3622-3631
Author(s):  
Victor V. Fedotov ◽  
Evgeny N. Ulomsky ◽  
Konstantin V. Savateev ◽  
Evgeny M. Mukhin ◽  
Denis A. Gazizov ◽  
...  

A highly efficient PASE approach to a new class of polycyclic purine derivatives has been proposed. The strategy includes a consecutive reduction, auto-aromatization, and heterocyclization of the initial nitrobenzimidazopyrimidines obtained by a three-component condensation. It was shown that reduction of nitrobenzimidazopyrimidines by metals in acidic media was more efficient than heterogeneous hydro­genation. Novel derivatives of benz[4,5]imidazo[1,2-a]purines were obtained­ in good yields and the proposed structure was confirmed by X-ray crystal structure analysis. The obtained convergent benzimidazopurines combine two relevant medicinal chemistry scaffolds – benz­imidazole and purine.


1980 ◽  
Vol 35 (9) ◽  
pp. 1075-1082 ◽  
Author(s):  
D. Fenske ◽  
H. Prokscha ◽  
P. Stock ◽  
H. J. Becher

With R2PSi(CH3)3 (R = C6H5, i-C3H7, t-C4H9) one Cl atom of 3,4-dichlor-5-methoxy-2(5 H)-furanon (1) is substituted by the R2P group. An x-ray crystal structure analysis of the phosphino derivative with R = C6H5 (2) it has shown that of the two Cl atoms in 1 only the β-position (to C= O) is substituted. The coordination chemistry of 2 and its bis- (diphenylphosphino) derivative (3) is studied by preparation of the compounds 2 · Mo(CO)5 and 3 · Mo(CO)4. With PdCl2 · 2 C6H5CN (2) gives a dinuclear complex [2 · PdCl2]2, with bridging Cl atoms. The structure is established by a comparison with the similar complex of PdCl2 and 2-chloro-diphenylphosphino-maleic acid dimethylestor, which was synthe­sized as a model compound and studied by x-ray crystal structure analysis.


1999 ◽  
Vol 23 (9) ◽  
pp. 578-579
Author(s):  
Rainer Schobert ◽  
Hermann Pfab ◽  
Jutta Böhmer ◽  
Frank Hampel ◽  
Andreas Werner

Racemates of (η3-allyl)tricarbonyliron lactone complex Fe(CO)3{η1:η3-C(O)XCH2CHCMeCH2} 1a (X = O) and (η3-allyl)tricarbonyliron lactam complex 2a (X = NMe) are resolved on a preparative scale by HPLC on cellulose tris(3,5-dimethylphenyl)carbamate/silica gel RP-8 and the absolute configuration of (-)-2a is determined by X-ray crystal structure analysis.


2005 ◽  
Vol 88 (4) ◽  
pp. 731-750 ◽  
Author(s):  
Stefan Sahli ◽  
Brian Frank ◽  
W. Bernd Schweizer ◽  
François Diederich ◽  
Denise Blum-Kaelin ◽  
...  

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