136180-02-4Relevant academic research and scientific papers
A chemoenzymatic and fully stereocontrolled total synthesis of the antibacterial natural product (-)-platencin
Chang, Ee Ling,Schwartz, Brett D.,Draffan, Alistair G.,Banwell, Martin G.,Willis, Anthony C.
, p. 427 - 439 (2015)
The natural product (-)-platencin is a potent antibacterial agent that exerts its effects through a novel mode of action. As such, it is an important lead in the development of next-generation antibacterials that are urgently needed because of the rapidly developing resistance to current therapies. The work reported here concerns the development of a convergent and chemoenzymatic total synthesis of (-)-platencin by methods that should provide access to a range of biologically relevant analogues. The key step involves a thermally promoted and facially selective intramolecular Diels-Alder (IMDA) cycloaddition reaction to give an adduct that embodies the tricarbocyclic core of (-)-platencin. This adduct was elaborated over thirteen steps to the natural product. The substrate for the IMDA reaction was prepared by Stille cross-coupling of a Z-configured alkenylstannane with an iodinated diene obtained in an enantiomerically pure form through the whole-cell biotransformation of iodobenzene.
Studies on taxane synthesis. III. Stereocontrolled synthesis of a twelve-membered lactam sulfide as a precursor of 4,8,11,11-tetramethyl-3-oxobicyclo[5.3.1]undec-8-ene
Ohtsuka,Oishi
, p. 1359 - 1364 (2007/10/02)
Stereocontrolled synthesis of two twelve-membered lactam sulfides 37 and 38 as precursors of 8,11,11-trimethyl-3-oxobicyclo[5.3.1]undec-8-enes constituting the A and B rings of taxane-diterpenes was achieved. The key step involves a Diels-Alder reaction o
