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Synfacts 2017; 13(09): 0895
DOI: 10.1055/s-0036-1590751
DOI: 10.1055/s-0036-1590751
Synthesis of Natural Products and Potential Drugs
Synthesis of (±)-Waihoensene
Further Information
Publication History
Publication Date:
18 August 2017 (online)
Significance
Isolated from a New Zealand podocarp in 1997, waihoensene is a tetracyclic diterpene with four contiguous quaternary carbon centers. Lee and co-workers report the first total synthesis of the title compound by employing a trimethylenemethane cycloaddition.
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Comment
Condensation of aldehyde F with tosylhydrazide followed by elimination, afforded diazoalkane G, which underwent the key tandem cycloaddition to afford tetracycle J. Four more steps completed the synthesis of (±)-waihoensene.
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