A Chemoenzymatic Total Synthesis of the Protoilludane Aryl Ester (+)-Armillarivin

A Chemoenzymatic Total Synthesis of the Protoilludane Aryl Ester (+)-Armillarivin

The title natural product, 1, has been synthesized in 20 steps from the enantiomerically pure cis-1,2-dihydrocatechol 2, itself obtained through the whole-cell biotransformation of toluene. The pivotal steps in the reaction sequence involve a Diels–Alder cycloaddition reaction between diene 2 and cy...

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Veröffentlicht in:Organic letters 2013-04, Vol.15 (8), p.1934-1937
Hauptverfasser: Schwartz, Brett D, Matoušová, Eliška, White, Richard, Banwell, Martin G, Willis, Anthony C
Format: Artikel
Sprache:eng
Schlagworte:
Biological Products - chemical synthesis
Biological Products - chemistry
Cyclopentanes - chemistry
Esters
Molecular Structure
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
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Zusammenfassung:The title natural product, 1, has been synthesized in 20 steps from the enantiomerically pure cis-1,2-dihydrocatechol 2, itself obtained through the whole-cell biotransformation of toluene. The pivotal steps in the reaction sequence involve a Diels–Alder cycloaddition reaction between diene 2 and cyclopentenone (3) and the photochemically promoted 1,3-acyl rearrangement of the bicyclo[2.2.2]oct-4-en-1-one 20 derived from the cycloadduct 4.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400583c