Synfacts 2017; 13(09): 0895
DOI: 10.1055/s-0036-1590751
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Waihoensene

Contributor(s): Erick M. Carreira, Matthieu J. R. Richter
Lee H. Kang T. Lee H.-Y. * Korea Advanced Institute of Science and Technology, Daejeon, Republic of Korea
Total Synthesis of (±)-Waihoensene.

Angew. Chem. Int. Ed. 2017;
56: 8254-8257
Further Information

Publication History

Publication Date:
18 August 2017 (online)

 
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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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