One-Pot Selective Homodimerization/Hydrogenation Strategy for Sequential Dicarba Bridge Formation

The installation of interlocked dicarba bridges into peptide sequences requires the development of a regioselective and chemoselective methodology. This manuscript describes a one-pot, chemoselective synthesis of three 2,7-diaminosuberic acid derivatives from an alkyne, a cobalt–carbonyl protected alkyne, and an alkene using metathesis and homogeneous hydrogenation catalysis

Cross-Metathesis Approach to the Tricyclic Marine Alkaloids (−)-Fasicularin and (−)-Lepadiformine A

A cross-metathesis protocol has been developed to provide facile access to highly hindered trisubstituted α-branched olefins, which when coupled with a cationic azaspirocyclization reaction, generates the marine alkaloids (−)-fasicularin <b>2</b> and a pro-forma synthesis of (−)-lepadiformine A <b>1</b>

A Formal Synthesis of (−)-Perhydrohistrionicotoxin Using a Cross Metathesis–Hydrogenation Approach

The development of an efficient, high yielding six-step convergent synthesis of the semisynthetic alkaloid (−)-perhydrohistrionicotoxin is described. The key transformations include the cross metathesis of a Brønsted-acid masked primary homoallylic amine with a vinyl cyclohexenone and a regioselective palladium catalyzed hydrogenation. This sequence generated the advanced Winterfeldt spirocyclic precursor in 47% overall yield, with a longest linear sequence of five steps