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Synfacts 2017; 13(05): 0449
DOI: 10.1055/s-0036-1590221
DOI: 10.1055/s-0036-1590221
Synthesis of Natural Products and Potential Drugs
Concise Total Synthesis of (±)-Verrubenzospirolactone
Lam HC.
Pepper HP.
Sumby CJ.
George JH.
* University of Adelaide, Australia
Biomimetic Total Synthesis of (±)-Verrubenzospirolactone.
Angew. Chem. Int. Ed. 2017;
DOI: 10.1002/anie.201700114.
Biomimetic Total Synthesis of (±)-Verrubenzospirolactone.
Angew. Chem. Int. Ed. 2017;
DOI: 10.1002/anie.201700114.
Further Information
Publication History
Publication Date:
18 April 2017 (online)
Key words
verrubenzospiro-lactone - Diels–Alder reaction - Knoevenagel condensation - oxa-6π-electro-cyclization
Significance
Isolated from Sinularia verruca, verrubenzospirolactone possesses a unique pentacyclic structure featuring a spirocyclic butenolide and five contiguous stereocenters. The target was synthesized in five steps, including a biomimetic intramolecular Diels–Alder cycloaddition.
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Comment
Readily available methylhydroquinone (A) was condensed with citral (B) in a Knoevenagel condensation–electrocyclization sequence. Oxidation, olefination, and isomerization of the resulting 2H-chromene C yielded the Z and E isomers of E, both of which underwent an intramolecular Diels–Alder cycloaddition to form (±)-verrubenzospirolactone and its diastereoisomer G, respectively.
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