Stereoselective Synthesis of 1,3-Amino Alcohols by the Pd-Catalyzed Cyclization of Trichloroacetimidates

The synthesis of 4-vinyl-5,6-dihydro-1,3-oxazines, precursors of 1,3-amino alcohols, using the palladium-catalyzed cyclization of trichloroacetimidates is reported. The reaction favors the formation of the 4,6-<i>cis</i>-isomers with up to >20:1 diastereoselectivity. Chemoselective hydrolysis of the resulting 5,6-dihydro-1,3-oxazines was also investigated

Total Synthesis of (±)-Cephalosol

A concise and efficient total synthesis of (±)-cephalosol has been completed (5 steps from known ester <b>5</b>, 39% overall yield), featuring a Cu(II)-promoted haloisocoumarin formation and sequential Suzuki cross-coupling/intramolecular oxo-Michael addition

Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki–Hiyama–Kishi Medium-Ring Formation

A total synthesis of the highly strained natural product aquatolide has been achieved. The synthesis featured a photoinduced Wolff ring contraction reaction for the construction of bicyclo[2.1.1]­hexane from diazo compound with a bicyclo[2.2.1]­heptane skeleton. The eight-membered enone was built by a late-stage intramolecular Nozaki–Hiyama–Kishi vinylation reaction of steric bulky vinyl iodide and aldehyde