Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework
Date
2018-10-25
Authors
Tang, Fei
Lan, Ping
Bolte, Benoit
Banwell, Martin
Ward, Jas
Willis, Anthony
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American Chemical Society
Abstract
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 title compound 4.
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Journal of Organic Chemistry
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Journal article
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Open Access
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