114050-31-6Relevant articles and documents
Unified synthesis of quinone sesquiterpenes based on a radical decarboxylation and quinone addition reaction
Ling, Taotao,Poupon, Erwan,Rueden, Erik J.,Kim, Sun H.,Theodorakis, Emmanuel A.
, p. 12261 - 12267 (2007/10/03)
A unified synthesis of several quinone sesquiterpenes is described herein. Essential to this strategy is a novel radical addition reaction that permits the attachment of a fully substituted bicyclic core 16 to a variably substituted quinone 10. The addition product 15 can be further functionalized, giving access to natural products with a high degree of oxygenation at the quinone unit. The quinone addition reaction is characterized by excellent chemoselectivity, taking place only at conjugated and unsubstituted double bonds, and regioselectivity, being strongly influenced by the resonance effect of heteroatoms located on the quinone ring. These features were successfully applied to the synthesis of avarol (1), avarone (2), methoxyavarones (4, 5), ilimaquinone (6), and smenospongidine (7), thereby demonstating the synthetic value of this new method.
An expeditious synthesis of chaetomellic anhydrides a and B, and analogues
Poigny, Stephane,Guyot, Michele,Samadi, Mohammad
, p. 2175 - 2177 (2007/10/03)
Chaetomellic anhydrides A and B and analogues have been prepared in one step by Barton radical decarboxylation; namely, irradiation of thiohydroxamic esters derived from carboxylic acids, in the presence of citraconic anhydride.
N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides
Barton, Derek H. R.,Ferreira, J. Albert
, p. 9347 - 9366 (2007/10/03)
The reaction between an acyl derivative of N-hydroxypyridine-2(1H)- thione (a Barton PTOC ester) and either an amine (primary or secondary), or the corresponding sulfenamide, led to the formation of a carboxamide in a clean transformation requiring minimal work-up and purification. The reaction with a sulfenamide is particularly useful since the only by-product, an unsymmetrical disulfide, is of both synthetic and biological value. In sterically demanding cases, Barton PTOC esters were more reactive towards benzenesulfenamides than to the corresponding free amines.