347840-66-8Relevant articles and documents
Total synthesis of the quinone epoxide dimer (+)-torreyanic acid: Application of a biomimetic oxidation/electrocyclization/Diels-Alder dimerization cascade
Li, Chaomin,Johnson, Richard P.,Porco Jr., John A.
, p. 5095 - 5106 (2007/10/03)
An asymmetric synthesis of the quinone epoxide dimer (+)-torreyanic acid (48) has been accomplished employing [4 + 2] dimerization of diastereomeric 2H-pyran monomers. Synthesis of the related monomeric natural product (+)-ambuic acid (2) has also been achieved which establishes the biosynthetic relationship between these two natural products. A tartrate-mediated nucleophilic epoxidation involving hydroxyl group direction facilitated the asymmetric synthesis of a key chiral quinone monoepoxide intermediate. Thermolysis experiments have also been conducted on a model dimer based on the torreyanic acid core structure and facile retro Diels-Alder reaction processes and equilibration of diastereomeric 2H-pyrans have been observed. Theoretical calculations of Diels-Alder transition states have been performed to evaluate alternative transition states for Diels-Alder dimerization of 2H-pyran quinone epoxide monomers and provide insight into the stereocontrol elements for these reactions.
Exploring Chemical Diversity of Epoxyquinoid Natural Products: Synthesis and Biological Activity of (-)-Jesterone and Related Molecules
Hu, Yongbo,Li, Chaomin,Kulkarni, Bheemashankar A.,Strobel, Gary,Lobkovsky, Emil,Torczynski, Richard M.,Porco Jr., John A.
, p. 1649 - 1652 (2007/10/03)
(matrix presented) Enantioselective syntheses of the potent antifungal agent (-)-jesterone, its hydroxy epimer, and a dimeric quinone epoxide derivative are reported. The synthesis involves diastereoselective epoxidation of a chiral quinone monoketal deri
