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Total Synthesis of the Pentacyclic Diterpenoid Tropone Hainanolidol

Frey, Barbara; Wells, Adam; Roden, Francis; Au, Ty; Hockless, David; Willis, Anthony; Mander, Lewis


The total synthesis of the unusual diterpenoid tropone, hainanolidol (1), discovered in the bark of the yew species, Cephalotaxus hainanensis, has been completed in 26 steps from 3,5-dimethylanisole. The intramolecular cyclopropanation reaction of the aryl ring in (30) by means of the rhodium mandelate-catalysed reaction of the diazoacetyl function was used to assemble the 5/7 ring system of (31), at the same time elaborating a cycloheptatriene moiety that could be transformed subsequently to...[Show more]

CollectionsANU Research Publications
Date published: 2000
Type: Journal article
Source: Australian Journal of Chemistry
DOI: 10.1071/CH00124


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