697302-70-8Relevant academic research and scientific papers
Synthesis and evaluation of the analogues of penicillide against cholesterol ester transfer protein
Zhang, Qiao,Deng, Chunlin,Fang, Lisong,Xu, Wenwei,Zhao, Qun,Zhang, Jiange,Wang, Yiping,Lei, Xinsheng
, p. 355 - 370 (2013/08/22)
A series of penicillide analogues, with modifications at C-3 and C-9 positions, are synthesized as potential cholesteryl ester transfer protein (CETP) inhibitors. The preliminary in vitro inhibition assay provided some valuable structure-activity relationship information about penicillide. Copyright
A convergent approach to dibenzodioxocinones: Synthesis of racemic penicillide
Deng, Chun-Lin,Zhang, Qiao,Fang, Lisong,Lei, Xinsheng,Lin, Guoqiang
, p. 626 - 635 (2012/05/20)
A convergent approach to dibenzodioxocinones was explored, thereby racemic penicillide ((±)-1a) could be obtained in 13 steps in 4.2% overall yield, based on 5-amino-2-methylphenol (5) (Schemes 2-4).
Synthesis of reblastatin, autolytimycin, and non-benzoquinone analogues: Potent inhibitors of heat shock protein 90
Wrona, Iwona E.,Gozman, Alexander,Taldone, Tony,Chiosis, Gabriela,Panek, James S.
supporting information; experimental part, p. 2820 - 2835 (2010/08/05)
A full account of an asymmetric synthesis of reblastatin (1) and the first total synthesis of autolytimycin (2) and related structural compounds is described. The syntheses expand the utility of a highly regio- and diastereoselective hydrometalation aldehyde addition sequence to assemble the fully functionalized ansa chain of the natural products. Also documented is an intramolecular copper-mediated amidation reaction to close the 19-membered macrolactams. The amidation reaction was also employed for the generation of structural derivatives (6-9) of phenolic ansamycins. Ansamycin natural products and selected structural analogues were evaluated in a competitive binding assay to breast cancer cell lysate and a cytotoxicity assay. Both reblastatin (1) and autolytimycin (2) were shown to bind the heat shock protein 90 with enhanced binding activity (～25 nM) than 17-allylamino-17-demethoxygeldanamycin (17-AAG, 4), a geldanamycin (3) derivative currently under evaluation for treatment of cancer (～100 nM).
Total synthesis of reblastatin
Wrona, Iwona E.,Gabarda, Ana E.,Evano, Gwilherm,Panek, James S.
, p. 15026 - 15027 (2007/10/03)
Enantioselective total synthesis of reblastatin is described. The synthesis highlights hydrozirconation, transmetalation, aldehyde addition sequence to install E-trisubstituted olefin and C7 stereocenter, and the first use of an intramolecular Buchwald-like amidation reaction to close the 19-membered macrolactam. Copyright
Biomimetically Inspired Total Synthesis and Structure Activity Relationships of 1-O-Methyllateriflorone. 6π Electrocyclizations in Organic Synthesis
Nicolaou,Sasmal, Pradip K.,Xu, Hao
, p. 5493 - 5501 (2007/10/03)
The total synthesis of 1-O-methyllateriflorone (2) is described. The construction of the cage-like domain of the molecule involved a biomimetic Claisen/Diels-Alder cascade, whereas the novel spiroxalactone framework was generated by an intramolecular Mich
Total synthesis of 1-O-methyllateriflorone
Nicolaou,Sasmal, Pradip K.,Xu, Hao,Namoto, Kenji,Ritzen, Andreas
, p. 4225 - 4229 (2007/10/03)
The unique spiroxalactone framework of lateriflorone (1) consists of a prenylated dihydrobenzoquinone moiety and a trioxatetracyclotetradecane system. A tandem Claisen rearrangement/Diels-Alder cascade was the key step in the synthesis of the complex tetr
