Total syntheses of (−)-15-oxopuupehenol and (+)-puupehenone and formal syntheses of (−)-puupehenol and (+)-puupehedione,Organic Chemistry Frontiers

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Total syntheses of (−)-15-oxopuupehenol and (+)-puupehenone and formal syntheses of (−)-puupehenol and (+)-puupehedione
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2019-11-15 , DOI: 10.1039/c9qo01027k
Huayue Song _{1,

2,

3,

4,

5} , Lin Liu _{1,

2,

3,

4,

5} , Mingyang Yang _{1,

2,

3,

4,

5} , Guangmiao Wu _{1,

2,

3,

4,

5} , Peng Chen _{1,

2,

3,

4,

5} , Xingang Xie _{1,

2,

3,

4,

5} , Xuegong She _{1,

2,

3,

4,

5}

Affiliation

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.

中文翻译：

（-）-15-氧杂戊烯酚和（+）-puupehenone的总合成以及（-）-puupehenol和（+）-puupehedione的形式合成

通过8个步骤（最长的线性途径）已完成了抗肿瘤和抗疟疾海洋海绵代谢物（-）-15-氧代普萘酚的简明全合成，R -（-）-香芹酮的总收率为18％。我们的合成涉及Suzuki羰基化偶联反应，以组装紧密的四取代的α，β-不饱和芳基酮和KOH促进的分子内环化反应，以构建独特的苯并二氢吡喃酮核。该抗结核药（+）-puupehenone通过三步转化法从合成的（-）-15-oxopuupehenol中获得。（-）-puupehenol和（+）-puupehedione的形式合成也可以从相同的高级中间体19中获得。

更新日期：2019-11-15

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