35458-39-0Relevant articles and documents
Dehydrogenative coupling to enable the enantioselective total synthesis of (-)-simaomicin α
Wang, Yizhong,Wang, Chao,Butler, John R.,Ready, Joseph M.
, p. 10796 - 10799 (2013)
The anticancer natural product simaomicin α has been synthesized. Asymmetric synthesis allowed the assignment of absolute stereochemistry. The enantiomer of the naturally occurring substance shows potent cytotoxicity towards Gram-positive bacteria and human cancer cells. Bn=benzyl, BOM=benzyloxymethyl. Copyright
Process Development and Scale-up of Fully Synthetic Tetracycline TP-2758: A Potent Antibacterial Agent with Excellent Oral Bioavailability
Zhang, Wu-Yan,Sun, Cuixiang,Hunt, Diana,He, Minsheng,Deng, Yonghong,Zhu, Zhijian,Chen, Chi-Li,Katz, Christopher E.,Niu, John,Hogan, Philip C.,Xiao, Xiao-Yi,Dunwoody, Nicholas,Ronn, Magnus
, p. 284 - 296 (2016/03/04)
Process research and development of the fully synthetic broad spectrum tetracycline TP-2758, with a chiral pyrrolidine side chain at the C-8 position, is described. The process utilizes two key intermediates, 7 and 10, in a convergent approach that allows for manufacturing of sufficient quantities of API to supply preclinical and early clinical development. The pyrrolidine moiety was introduced into the left-hand piece (LHP) 10 with high enantioselectivity using Ellman's sulfinamide chemistry, and the absolute configuration was confirmed by X-ray crystal structure analysis.
Enantioselective total synthesis of ( - )-kibdelone C
Butler, John R.,Wang, Chao,Bian, Jianwei,Ready, Joseph M.
supporting information; experimental part, p. 9956 - 9959 (2011/08/21)
The kibdelones are aromatic polyketide natural products featuring isoquinolinone and tetrahydroxanthone ring systems. They display potent cytotoxicity toward a range of human cancer cell lines. Here, we present an enantioselective total synthesis of kibdelone C that utilizes a Shi epoxidation to establish the absolute and relative stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C - H arylation to complete the hexacyclic skeleton.