Oxidative Decarboxylation as a Route to Ketene Acetals:  Assignment of Relative and Absolute Stereochemistry to the Fungal Metabolite Benesudon by Total Synthesis

2007 ◽  
Vol 9 (25) ◽  
pp. 5315-5317 ◽  
Author(s):  
Derrick L. J. Clive ◽  
Minaruzzaman
Keyword(s):  
Total Synthesis ◽  
Oxidative Decarboxylation ◽  
Fungal Metabolite ◽  
Ketene Acetals ◽  
Absolute Stereochemistry

ChemInform Abstract: The First Total Synthesis of N1999-A2: Absolute Stereochemistry and Stereochemical Implications into DNA Cleavage.

ChemInform ◽  
2010 ◽  
Vol 33 (14) ◽  
pp. no-no
Author(s):  
Shoji Kobayashi ◽  
Shukuko Ashizawa ◽  
Yusuke Takahashi ◽  
Yukio Sugiura ◽  
Makoto Nagaoka ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Dna Cleavage ◽  
Absolute Stereochemistry

scholarly journals Synthetic study of ravidomycin, a hybrid natural product

2000 ◽  
Vol 72 (9) ◽  
pp. 1783-1786 ◽  
Author(s):  
Keisuke Suzuki
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Amino Sugar ◽  
Antitumor Antibiotics ◽  
Ready Availability ◽  
Silyl Acetals ◽  
Gilvocarcin V ◽  
Absolute Stereochemistry

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.

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