72615-20-4Relevant academic research and scientific papers
Stereocontrolled Synthesis of (-)-Bactobolin A
Vojá?ková, Petra,Michalska, Lucyna,Ne?as, Marek,Shcherbakov, Dimitri,B?ttger, Erik C.,?poner, Ji?í,?poner, Judit E.,?venda, Jakub
supporting information, p. 7306 - 7311 (2020/05/25)
A stereoselective synthesis of the ribosome-binding antitumor antibiotic (-)-bactobolin A is reported. The presented approach makes effective use of (-)-quinic acid as a chiral pool starting material and substrate stereocontrol to establish the five contiguous stereocenters of (-)-bactobolin A. The key steps of the synthesis include a stereoselective vinylogous aldol reaction to introduce the unusual dichloromethyl substituent, a completely diastereoselective rhodium(II)-catalyzed C-H amination reaction to set the configuration of the axial amine, and an intramolecular alkoxycarbonylation to build the bicyclic lactone framework. The developed synthetic route was used to prepare 90 mg of (-)-bactobolin A trifluoroacetate in 10% overall yield.
Stereoselective total syntheses of the antitumor antibiotics (+)-actinobolin and (-)-bactobolin from a common bridged lactone intermediate
Garigipati,Tschaen,Weinreb
, p. 3475 - 3482 (2007/10/02)
Efficient, highly steroselective approaches have been developed to (+)-actinobolin (1) and (-)-bactobolin (3) from bridged α-keto lactone 11, which can be readily prepared via intramolecular SnCl4 catalyzed ene reaction of cyclohexenol glyoxyla
Stereoselective Total Synthesis of the Antitumor Antibiotic (-)-Bactobolin
Garigipati, Ravi S.,Weinreb, Steven M.
, p. 4143 - 4145 (2007/10/02)
The first total synthesis of the biologically active microbial metabolite bactobolin (2) has been achieved.An efficient, stereoselective route to 2 in 16 steps from previously prepared α-keto lactone 3 is outlined.
