Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks.
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.
Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.
Kerrie A B
KA
Austin
Jon D
JD
Elsworth
Martin G
MG
Banwell
Anthony C
AC
Willis
D000929:Antidepressive Agents, Tricyclic / Q000138:chemical synthesis; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004789:Enzyme Activation; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009795:Octanes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*
D000929:Antidepressive Agents, Tricyclic; D001643:Bridged Bicyclo Compounds; D009795:Octanes; D013729:Terpenes; C026728:octane