174627-70-4Relevant academic research and scientific papers
Diverted total synthesis of the baulamycins and analogues reveals an alternate mechanism of action
Steele, Andrew D.,Ernouf, Guillaume,Lee, Young Eun,Wuest, William M.
, p. 1126 - 1129 (2018/02/23)
The baulamycins were identified as in vitro siderophore biosynthesis inhibitors. Diverted total synthesis was used to construct the natural products and eight strategic analogues, three of which had improved inhibitory activity. Biological testing then revealed that membrane damage is the predominant mode of action in Staphylococcus aureus cells.
Structural Revision of Baulamycin A and Structure-Activity Relationships of Baulamycin A Derivatives
Sengupta, Sandip,Bae, Munhyung,Oh, Dong-Chan,Dash, Uttam,Kim, Hak Joong,Song, Woon Young,Shin, Injae,Sim, Taebo
, p. 12947 - 12966 (2017/12/26)
Total synthesis of the proposed structure of baulamycin A was performed. The spectral properties of the synthetic compound differ from those reported for the natural product. On the basis of comprehensive NMR study, we proposed two other possible structur
Divergent enantioselective total synthesis of siphonarienal, siphonarienone, and pectinatone
Yadav, Jhillu Singh,Chary, D. Narasimha,Yadav, Nagendra Nath,Sengupta, Sandip,Subba Reddy, Basi V.
, p. 1968 - 1977 (2013/11/06)
A divergent synthesis of siphonarienal, siphonarienone, and pectinatone has been achieved from a common precursor 4, which was synthesized by using an enzymatic desymmetrization approach. The major key steps involved were Grignard reaction, Wittig reactio
Catalytic, efficient, and syn-selective construction of deoxypolypropionates and other chiral compounds via Zr-catalyzed asymmetric carboalumination of allyl alcohol
Liang, Bo,Novak, Tibor,Tan, Ze,Negishi, Ei-Ichi
, p. 2770 - 2771 (2007/10/03)
An efficient, syn-selective, all catalytic asymmetric protocol for the synthesis of α,ω-diheterofunctional deoxypolypropionates via Zr-catalyzed asymmetric carboalumination (ZACA reaction) was developed. The success of the method critically hinges on the
Synthetic studies on borrelidin: enantioselective synthesis of the C1-C12 fragment.
Vong, Binh G,Abraham, Sunny,Xiang, Alan X,Theodorakis, Emmanuel A
, p. 1617 - 1620 (2007/10/03)
[structure: see text] An efficient, enantioselective synthesis of the C1-C12 fragment 2 of borrelidin is presented. Construction of the "skipped" polymethylene chain of 2 was accomplished by iteration of Myers' alkylation, while formation of the C3 stereocenter was achieved by Roush's asymmetric allylboration methodology.
Synthesis of (+)-siphonarienone: Asymmetric alkylation using a chiral benzopyrano-isoxazolidine auxiliary
Abiko, Atsushi,Masamune, Satoru
, p. 1081 - 1084 (2007/10/03)
Asymmetric alkylation of the potassium enolates derived from N-propionyl benzopyrano[4,3-c]-isoxazolidine derivatives with chiral alkyl triflates proceeded smoothly with high diastereoselectivity. The stereochemistry of the newly formed stereogenic center was fully controlled by the facial selectivity of the enolate according to the rule of double asymmetric synthesis. The application of this methodology led to the first synthesis of (+)-siphonarienone, a marine polypropionate natural product.
