98263-92-4Relevant articles and documents
"mirror-image" manipulation of curdione stereoisomer scaffolds by chemical and biological approaches: Development of a sesquiterpenoid library
Qin, Bin,Li, Yuxin,Meng, Lingxin,Ouyang, Jingping,Jin, Danni,Wu, Lei,Zhang, Xin,Jia, Xian,You, Song
, p. 272 - 278 (2015/04/22)
The sesquiterpenoid curdione is one of the main bioactive components in the essential oil of Rhizoma Curcumae (Curcuma wenyujin, Curcuma phaeocaulis, and Curcuma kwangsiensis), which has been clinically used for the treatment of cancer in mainland China. Recently it was reported that natural curdione could be hydroxylated by Aspergillus niger and transferred to its corresponding curcumalactones under acidic conditions. Based on this study, the development of a sesquiterpenoid library through the "mirror-image" manipulation of bioactive (non)natural curdione scaffolds by chemical and biological approaches is presented herein. A. niger induced the hydroxylation of two pairs of curdione enantiomers, yielding the corresponding mirror-image hydroxylated curdiones. Simultaneously, the acid-mediated intramolecular "ene" rearrangements of these curdiones and hydroxylated curdione enantiomers yielded the corresponding mirror-image curcumalactones and hydroxylated curcumalactones. Among the 16 pairs of enantiomers obtained in this study, 23 compounds are new sesquiterpenoids. These curdione and curcumalactone derivatives are of particular interest, as they have the potential to be used as lead compounds and scaffolds in drug discovery.
Dyotropic rearrangements of fused tricyclic β-lactones: Application to the synthesis of (-)-curcumanolide A and (-)-curcumalactone
Leverett, Carolyn A.,Purohit, Vikram C.,Johnson, Alex G.,Davis, Rebecca L.,Tantillo, Dean J.,Romo, Daniel
, p. 13348 - 13356 (2012/09/22)
Dyotropic rearrangements of fused, tricyclic β-lactones are described that proceed via unprecedented stereospecific, 1,2-acyl migrations delivering bridged, spiro-γ-butyrolactones. A unique example of this dyotropic process involves a fused bis-lactone possessing both β- and δ-lactone moieties which enabled rapid access to the core structures of curcumanolide A and curcumalactone. Our current mechanistic understanding of the latter dyotropic process, based on computational studies, is also described. Other key transformations in the described divergent syntheses of (-)-curcumanolide A and (-)-curcumalactone from a common intermediate (11 and 12 steps from 2-methyl-1,3-cyclopentanedione, respectively), include a catalytic, asymmetric nucleophile (Lewis base)-catalyzed aldol-lactonization (NCAL) leading to a tricyclic β-lactone, a Baeyer-Villiger oxidation in the presence of a β-lactone, and highly facial-selective and stereocomplementary reductions of an intermediate spirocyclic enoate. The described dyotropic rearrangements significantly alter the topology of the starting tricyclic β-lactone, providing access to complex spirocyclic cyclopentyl-γ-lactones and bis-γ-lactones in a single synthetic operation.
THE ABSOLUTE CONFIGURATION OF CURDIONE AND THE STEREOSTRUCTURE OF CURCUMALACTONE FROM CURCUMA WENYUJIN
Inayama, Seiichi,Gao, Ji-Fu,Hariyama, Kenzo,Hikichi, Manabu,Iitaka, Yoichi,et al.
, p. 2179 - 2182 (2007/10/02)
The absolute configuration of curdione isolated from Curcuma wenyujin was determined as 1 on the basis of its CD spectra and the X-ray diffraction of the p-bromobenzoate of 8αH-dihydrocurdione (2a).The absolute stereostructure of a new spirocyclopentanolide, curcumalactone occuring in the titled plant, was deduced as 3 based on its direct X-ray analysis and the biomimetic transformation of 1 to 3.
