Total synthesis of peshawaraquinone through late-stage [3+2] cycloaddition or α-ketol rearrangement

被引：0

作者：

Guo, Huihui ^{[1
,2
]}

Ren, Li ^{[1
]}

Sang, Xueli ^{[1
]}

Lu, Xuena ^{[1
]}

Li, Tian ^{[1
]}

Zhou, Wenming ^{[1
]}

Rauf, Abdur ^{[3
]}

Hao, Hong-Dong ^{[1
,2
]}

机构：

[1] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, Yangling 712100, Shaanxi, Peoples R China

[2] Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncogen, Guangdong Prov Key Lab Chem Genom, Shenzhen 518055, Guangdong, Peoples R China

[3] Univ Swabi, Dept Chem, Anbar 23561, Khyber Pakhtunk, Pakistan

来源：

ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 04期

基金：

中国国家自然科学基金;

关键词：

BIOMIMETIC SYNTHESIS; ALLYLIC ALCOHOLS; CONVERSION; TERPENES;

D O I：

10.1039/d3qo01845h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two synthetic approaches to peshawaraquinone, an uncommon and complex naphthoquinone meroterpenoid, are described. Key to the success of these synthetic pathways includes HFIP-promoted metal-free allylation to couple lawsone with allylic alcohols, together with an organo-catalyzed [3 + 2] cycloaddition for constructing the bicyclo[3.2.1]octane core structure. A [2 + 2] photocycloaddition/alpha-ketol rearrangement sequence was also applied as an alternative approach to peshawaraquinone. Further investigation revealed that natural peshawaraquinone is a racemate. Two synthetic approaches to peshawaraquinone, an uncommon and complex naphthoquinone meroterpenoid, are described.

引用

页码：1084 / 1089

页数：6

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