14090-22-3Relevant academic research and scientific papers
A Concise Enantioselective Total Synthesis of (?)-Virosaine A
Hughes, Jonathan M. E.,Gleason, James L.
, p. 10830 - 10834 (2017)
The total synthesis of (?)-virosaine A (1) was achieved in ten steps starting from furan and 2-bromoacrolein. A one-pot Diels–Alder cycloaddition/organolithium addition initiated an efficient sequence to access a key oxime/epoxide intermediate. Heating this intermediate in acetic acid resulted in an intramolecular epoxide opening/nitrone [3+2] cycloaddition cascade to construct the caged core of 1 in a single step. Several methods of C?H functionalization were assessed on the cascade product, and ultimately, a directed lithiation/bromination effected selective C14 functionalization, enabling the synthesis of 1.
A bio-inspired cascade and a late-stage directed sp3 C–H lithiation enables a concise total synthesis of (?)-virosaine A
Hughes, Jonathan M.E.,Gleason, James L.
, p. 759 - 768 (2018)
The asymmetric total synthesis of (?)-virosaine A was achieved in 9% overall yield from commercially/readily available starting materials. Inspired by an intriguing biosynthetic proposal, a novel cascade reaction sequence was developed to efficiently cons
Highly enantioselective oxazaborolidine-catalyzed reduction of 1,3-dicarbonyl compounds: Role of the additive diethylaniline
Chein,Yeung,Corey
body text, p. 1611 - 1614 (2009/09/07)
The oxazaborolidine-catalyzed reduction of 2,2-disubstituted cycloalkan-1,3-diones or hindered 2,2-disubstituted cyclic ketones using catecholborane as reductant proceeds with greater enantioselectivity when N,N-diethylaniline is added. It has now been sh
Enantioselective synthesis of the core of banyaside, suomilide, and spumigin HKVV
Schindler, Corinna S.,Stephenson, Corey R. J.,Carreira, Erick M.
supporting information; experimental part, p. 8852 - 8855 (2009/05/30)
Concise: The first synthesis of the unique azabicyclononane core found in the aeruginosin class of serine protease inhibitors is described. The route is characterized by its efficiency (eight steps) and sets the stage for subsequent introduction of the gl
Novel Organoboron-Oxygen-Halogenaluminium Compounds from Triorganoboroxins with Aluminium Trihalides
Koester, Roland,Angermund, Klaus,Serwatowski, Janusz,Sporzynski, Andrzej
, p. 1301 - 1314 (2007/10/02)
4 mol of triorganoboroxins (RBO)3 (1) react with 6 mol of aluminium trihalides AlHal3 (2) under cleavage of 4 mol dihalogenoorganoboranes RBHal2 (3) leading in high yields to 2 mol of compounds 4 having the composition R4Al3B4Hal5O6 (MS analyses) .The structure of 4aa, 4ba, 4ca, and 4bb in solution is deduced from spectroscopic data (IR; 1H, 11B, 17O and 27Al NMR).The molecular structure of the solid (C6H5)4Al3B4Cl5O6 (4da) with two (AlOBOBO)-rings bonded through one penta-coordinated aluminium atom was determined by X-ray diffraction analysis.
