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Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework

Tang, Fei; Lan, Ping; Bolte, Benoit; Banwell, Martin; Ward, James; Willis, Anthony

Description

A total synthesis of the title sesquiterpene 4 is described that starts with the chiral, non-racemic cis-1,2-dihydrocatechol 10 obtained through the whole-cell biotransformation of p-iodotoluene. Compound 10 is elaborated over seven steps, including Negishi cross-coupling and intramolecular Diels–Alder (IMDA) cycloaddition reactions, to ketone 7 that engages in a photochemically promoted 1,3-acyl migration and so affording cyclobutanone 6. Compound 6 was converted over further steps into the...[Show more]

CollectionsANU Research Publications
Date published: 2018-10-25
Type: Journal article
URI: http://hdl.handle.net/1885/201573
Source: Journal of Organic Chemistry
DOI: 10.1021/acs.joc.8b02626

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