ARKIVOC 2016 21;2016(1):276-306. Epub 2016 Jun 21.
Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico, 88003, USA.
This account describes the historical development of the coupling of γ,δ-unsaturated Fischer carbene complexes and -alkynylbenzaldehydes, which directly affords hydrophenanthrene ring systems in a process where each reactant contributes five carbons to the newly-formed bicyclo[4.4.0]decane ring system. The process has been termed net [5+5] cycloaddition. Use of the reaction to produce various medicinally important natural products and/or their parent ring systems is discussed.