252577-53-0Relevant academic research and scientific papers
Enantioselective total synthesis of avarol and avarone
Ling, Taotao,Xiang, Alan X.,Theodorakis, Emmanuel A.
, p. 3089 - 3091 (1999)
Formation of the C11-C1' bond through application of Barton's radical decarboxylation and quinone addition is the cornerstone of a new convergent and concise synthesis of the marine metabolites avarol (1) and avarone (2; see scheme), for which antimitotic, antileukemic, and antiviral effects have been reported.
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.
