Stereoselective synthesis of five- and six-membered carbocycles <i>via</i> Matteson homologation/ring closing metathesis

Construction of eight-membered carbocycles with trisubstituted double bonds using the ring closing metathesis reaction.

Medium sized carbocycles are particularly difficult to synthesize. Ring closing metathesis reactions (RCM) have recently been applied to construct eight-membered carbocycles, but trisubstituted double bonds in the eight-membered rings are more difficult to produce using RCM reactions. In this review, model examples and our own results are cited and the importance of the preparation of suitably ...

Synthesis of five-membered osmacycloallenes and conversion into six-membered osmacycloallenes.

A stereoselective synthesis of (+)-physoperuvine using a tandem aza-Claisen rearrangement and ring closing metathesis reaction.

A stereoselective synthesis of (+)-physoperuvine, a tropane alkaloid from Physalis peruviana Linne has been developed using a one-pot tandem aza-Claisen rearrangement and ring closing metathesis reaction to form the key amino-substituted cycloheptene ring.

Pentafulvene-derived η3-allyltitanocenes as intermediates for the stereoselective functionalization of 5-membered carbocycles.

Allyltitanocene complexes can be generated by reacting pentafulvenes with DIBAL-H and Cp2TiCl2. Their coupling with aldehydes affords homoallylic alcohols in a highly regio- and stereoselective manner. The potential of this method for the stereoselective synthesis of cyclopentane derivatives is illustrated.

A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone via ring-closing metathesis

A short stereoselective synthesis of (+)-(6R,2'S)-cryptocaryalactone was successfully completed. Key steps included the application of Carreira's asymmetric alkynylation reaction to form a propargylic alcohol and subsequently lactone formation using the powerful ring-closing metathesis reaction.