Asymmetric Total Synthesis of Lancifodilactone G Acetate. 1. Diastereoselective Synthesis of CDEFGH Ring System.

The stereoselective construction of the CDEFGH ring system of lancifodilactone G is described. The key steps in this synthesis are (i) ring-closing metathesis for formation of the oxa-bridged eight-membered ring; (ii) an intramolecular Pauson-Khand reaction for construction of the sterically congested F ring; and (iii) sequential cross-metathesis, hydrogenation, and lactonization reactions for installation of the anomerically stabilized bis-spiro ketal fragment of lancifodilactone G.

Asymmetric Total Synthesis of Lancifodilactone G Acetate. 2. Final Phase and Completion of the Total Synthesis.

The asymmetric total synthesis of lancifodilactone G acetate was accomplished in 28 steps. The key steps in this synthesis include (i) an asymmetric Diels-Alder reaction for formation of the scaffold of the BC ring; (ii) an intramolecular ring-closing metathesis reaction for the formation of the trisubstituted cyclooctene using a Hoveyda-Grubbs II catalyst; (iii) an intramolecular Pauson-Khand reaction for construction of the sterically congested F ring; (iv) sequential cross-metathesis, hydrogenation, and lactonization reactions for installation of the anomerically stabilized bis-spiro ketal fragment of lancifodilactone G; and (v) a Dieckmann-type condensation reaction for installation of the A ring. The strategy and chemistry developed for the total synthesis will be useful in the synthesis of other natural products and complex molecules.

Asymmetric Total Synthesis of Lancifodilactone G Acetate.

Asymmetric total synthesis of structurally intriguing and highly oxygenated lancifodilactone G acetate (7) has been achieved for the first time in 28 steps from a cheap commodity chemical, 2-(triisopropylsiloxy)-1,3-butadiene.

Catalytic and Enantioselective Diels-Alder Reactions of (E)-4-Oxopent-2-enoates.

Novel oxazaborolidines activated by the strong acid triflimide or AlBr3 form cationic chiral catalysts. These are effective catalysts for highly regio- and enantioselective Diels-Alder reactions using substituted (E)-4-oxopent-2-enoates as dienophiles.

Conductivity enhancement of multiwalled carbon nanotube thin film via thermal compression method.

For the first time, the thermal compression method is applied to effectively enhance the electrical conductivity of carbon nanotube thin films (CNTFs). With the assistance of heat and pressure on the CNTFs, the neighbor multiwalled carbon nanotubes (CNTs) start to link with each other, and then these separated CNTs are twined into a continuous film while the compression force, duration, and temperature are quite enough for the reaction. Under the compression temperature of 400°C and the compression force of 100 N for 50 min, the sheet resistance can be reduced from 17 to 0.9 k Ω/sq for the CNTFs with a thickness of 230 nm. Moreover, the effects of compression temperature and the duration of thermal compression on the conductivity of CNTF are also discussed in this work.