SYNTHESES AND METAL MEDIATED REACTION CHEMISTRY OF 2-SILYL-1,3-DIENES

Asymmetric carbon-carbon bond forming processes and catalytic one-pot reactions remain challenges in organic synthesis. Since the discovery of the Diels-Alder reaction over eighty years ago, it has been one of the most important tools for synthetic organic chemists to synthesize as many as three carbocyclic rings in intermolecular and intramolecular reactions. Its versatility can provide up to four contiguous asymmetric centers with good yields. The majority of the Diels-Alder additions are endo selective, and reports of exo selective Diels-Alder reactions are few in the literature. Our goal is development of methodologies for catalytic, regioselective, exo selective, enantioselective Diels-Alder reactions and subsequent Hiyama-Denmark and Negishi cross couplings to make highly substituted cyclohexenoids with controlled relative and absolute stereochemistries. Diterpenoids containing the clerodane carbon skeleton are prevalent as secondary metabolites. Synthetic approaches to the trans-clerodanes are known, but cis-clerodanes are rare. This proposed methodology will also allow the scientific community to construct biologically important core structures like cis clerodanes and their derivatives.

Grantor dc:publisher

Wake Forest University

Year dc:date.issued

2015

Author dc:creator

• Choudhury, Partha Pratim

Language dc:language.iso

en

Handle dc:identifier.uri

http://hdl.handle.net/10339/57251

OAI identifier oai:identifier

oai:wakespace.lib.wfu.edu:10339/57251