Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks

Kerrie A B Austin; Jon D Elsworth; Martin G Banwell; Anthony C Willis

doi:10.1039/b921600f

Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks

Org Biomol Chem. 2010 Feb 21;8(4):751-4. doi: 10.1039/b921600f. Epub 2009 Dec 7.

Authors

Kerrie A B Austin¹, Jon D Elsworth, Martin G Banwell, Anthony C Willis

Affiliation

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.

PMID: 20135028
DOI: 10.1039/b921600f

Abstract

New and simple protocols are described for the conversion of the enzymatically-derived and enantiomerically pure cis-1,2-dihydrocatechol (X = I) and its 6-methylated derivative into either antipodal form of compounds embodying the tricyclic frameworks of terpenoids . Key steps include intramolecular Diels-Alder (IMDA) and (in some cases) singlet or triplet-based photochemical processes.

MeSH terms

Antidepressive Agents, Tricyclic / chemical synthesis
Bridged Bicyclo Compounds / chemistry*
Catalysis*
Cyclization
Enzyme Activation
Models, Chemical
Models, Molecular
Molecular Structure
Octanes / chemical synthesis*
Stereoisomerism*
Terpenes / chemistry*

Substances

Antidepressive Agents, Tricyclic
Bridged Bicyclo Compounds
Octanes
Terpenes
octane