35019-66-0Relevant articles and documents
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 (2015/02/05)
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.
New chiral iminium salt catalysts for asymmetric epoxidation
Bulman Page, Philip C.,Buckley, Benjamin R.,Rassias, Gerasimos A.,Blacker, A. John
, p. 803 - 813 (2007/10/03)
A range of enantiomerically pure 4-substituted 5-amino-1,3-dioxanes has been condensed with 2-(2-bromoethyl)benzaldehyde to produce chiral dihydroisoquinolinium salts, which are effective asymmetric catalysts for the epoxidation of simple alkenes, giving ees of up to 71 %. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
AN IMPROVED SYNTHESIS OF (4S,5S)-2,2-DIMETHYL-4-PHENYL-1,3-DIOXAN-5-AMINE
Nordin, Ivan C.,Thomas, James A.
, p. 5723 - 5724 (2007/10/02)
The title compound is prepared in 78percent yield using an improved one-pot procedure which does not require final purification.