The [5+5] route to the phenanthrene skeleton.

Authors:
James W Herndon
James W Herndon
New Mexico State University
Mexico

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.

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Source
http://dx.doi.org/10.3998/ark.5550190.p009.611DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5340207PMC
June 2016
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