220254-16-0Relevant articles and documents
Toward the total synthesis of klaivanolide: Complete reinterpretation of its originally assigned structure
Ferrié, Laurent,Ferhi, Sabrina,Bernadat, Guillaume,Figadère, Bruno
, p. 6183 - 6189 (2014)
Klaivanolide is an antiparasitic natural product isolated from Uvaria klaineana, whose structure was originally assigned as a seven-membered lactone ring. Attempts towards the total synthesis of klaivanolide led us to revise its original structural assignment based on both experimental evidence and spectroscopic data. The isolated compound was revealed to be a known molecule, acetylmelodorinol, originally isolated from Melodorum fruticosum. Vibrational circular dichroism simulation of the reassigned structure was also performed to reinvestigate our previous studies on the determination of the absolute configuration of klaivanolide.
Stereocontrolled assembly of cis or trans angularly substituted hydrindenes by the unactivated intramolecular Diels-Alder reaction
Taber, Douglass F.,Song, Ying
, p. 7508 - 7512 (2007/10/03)
The unactivated intramolecular Diels-Alder reaction has become a powerful tool for the construction of polycyclic natural products. Nevertheless, the factors that govern diastereoselectivity in these cyclizations have not been fully understood. We here report that through the choice of the proper substituents, it is possible to make the unactivated intramolecular Diels-Alder reaction proceed to give either the cis angularly-substituted hydrindene 12b or the trans product 19a.
