Laurencia natural products. Part I. Crystal structure and absolute stereochemistry of laurencin

Author(s):  
A. Forbes Cameron ◽  
K. K. Cheung ◽  
G. Ferguson ◽  
J. Monteath Robertson
1977 ◽  
Vol 18 (35) ◽  
pp. 2998
Author(s):  
Joyce A. McMillan ◽  
Iain C. Paul ◽  
Salvatore Caccamese ◽  
Kenneth L. Rinehart

2000 ◽  
Vol 72 (9) ◽  
pp. 1783-1786 ◽  
Author(s):  
Keisuke Suzuki

Strategies and tactics associated with the total synthesis of hybrid natural products are discussed. The target is ravidomycin (2), one of the gilvocarcin-class antitumor antibiotics with an aryl C-glycoside structure. The first total synthesis of 2, which was achieved along similar lines of that of gilvocarcin V (1), served for the determination of the relative as well as the absolute stereochemistry of 2. Also revealed was a limitation of the synthetic scheme so long as the amino sugar congener was concerned. A preliminary result is discussed on the [2+2+2] approach that relies on the ready availability of various benzocyclobutene derivatives via regioselective [2+2] cycloaddition of α-alkoxybenzynes and ketene silyl acetals.


Tetrahedron ◽  
1987 ◽  
Vol 43 (20) ◽  
pp. 4777-4784 ◽  
Author(s):  
G. Cimino ◽  
S. De Rosa ◽  
S. De Stefano ◽  
R. Puliti ◽  
G. Strazzullo ◽  
...  

1976 ◽  
Vol 17 (47) ◽  
pp. 4219-4222 ◽  
Author(s):  
Joyce A. McMillan ◽  
Iain C. Paul ◽  
Salvatore Caccamese ◽  
Kenneth L. Rinehart

1993 ◽  
Vol 115 (15) ◽  
pp. 6673-6679 ◽  
Author(s):  
Laurent A. Decosterd ◽  
Ian C. Parsons ◽  
Kirk R. Gustafson ◽  
John H. Cardellina ◽  
James B. McMahon ◽  
...  

1996 ◽  
Vol 59 (12) ◽  
pp. 1203-1204 ◽  
Author(s):  
Loïc Toupet ◽  
Jean-François Biard ◽  
Jean-François Verbist

2018 ◽  
Author(s):  
Akina Yoshizawa ◽  
Antonio Feula ◽  
Louise Male ◽  
Andrew G. Leach ◽  
John Fossey

A series of single enantiomer, 2,4-<i>cis</i>-disubstituted amino azetidines were synthesised and used as ligands for copper-catalysed Henry reactions of aldehydes with nitromethane. Optimisation of ligand substituents and the reaction conditions was conducted. The enantiomeric excess of the formed products was highest when alkyl aldehydes were employed in the reaction (>99% e.e.). The absolute stereochemistry of one representative azetidine derivative salt was determined by analysis of the Flack parameter of an XRD single crystal structure. The origin of selectivity in catalysis was investigated computationally, revealing the importance of the amino-substituent in determining the stereochemical outcome. A racemic platinum complex of a <i>cis</i>-disubstituted azetidine is examined by XRD single crystal structure analysis with reference to its steric parameters, and analogies to the computationally determined copper complex catalyst are drawn.<br>


1997 ◽  
Vol 50 (4) ◽  
pp. 391 ◽  
Author(s):  
Trevor W. Hambley ◽  
Walter C. Taylor ◽  
Stephen Toth

The absolute stereochemistry of aplyroseol-1 (1), a diterpenoid isolated from Aplysillarosea Barrois, has been established as (5S; 7R; 8S; 9R; 10S; 13R; 14R; 15R) by determining the crystal structure of the p-bromobenzoyl derivative (3) by X-ray diffraction methods. The structure was refined to a residual of 0·032 for 1451 independent observed reflections. The crystals are monoclinic, space group P 21, a 6·668(8), b 20·04(1), c 10·974(3) Å, β 98·04(7)°.


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