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

文献信息

发布日期 2019-11-15

DOI 10.1039/C9QO01027K

影响因子 5.281

作者

Huayue Song, Lin Liu, Mingyang Yang, Guangmiao Wu, Peng Chen, Xingang Xie, Xuegong She

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摘要

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.

期刊推荐

Nature Medicine

Journal of Saudi Chemical Society

Drug Discovery Today

Russian Journal of Bioorganic Chemistry

Organic Process Research & Development

Journal of Peptide Science

Chemical Communications

Russian Journal of Coordination Chemistry

New Journal of Chemistry

Acta Materialia

来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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来源期刊

Organic Chemistry Frontiers

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