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Total syntheses of (−)-15-oxopuupehenol and (+)-puupehenone and formal syntheses of (−)-puupehenol and (+)-puupehedione

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Abstract

A concise total synthesis of antitumor and antimalarial marine sponge metabolite (−)-15-oxopuupehenol has been accomplished in 8 steps (longest linear route) with an overall yield of 18% from R-(−)-carvone. Our synthesis involves a Suzuki carbonylative coupling reaction to assemble the compact tetra-substituted α,β-unsaturated aryl ketone and a KOH promoted intramolecular cyclization reaction to construct the unique chromanone core. The antituberculosis drug (+)-puupehenone is obtained via a three-step transformation from the synthetic (−)-15-oxopuupehenol. The formal syntheses of (−)-puupehenol and (+)-puupehedione can also be achieved from the same advanced intermediate 19.

Graphical abstract: Total syntheses of (−)-15-oxopuupehenol and (+)-puupehenone and formal syntheses of (−)-puupehenol and (+)-puupehedione

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Publication details

The article was received on 20 Aug 2019, accepted on 05 Nov 2019 and first published on 15 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01027K
Org. Chem. Front., 2020, Advance Article

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    Total syntheses of (−)-15-oxopuupehenol and (+)-puupehenone and formal syntheses of (−)-puupehenol and (+)-puupehedione

    H. Song, L. Liu, M. Yang, G. Wu, P. Chen, X. Xie and X. She, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01027K

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