A divergent approach to synthesize C7 epoxyquinones from (-)-shikimic acid

被引：0
|
作者：
Wu, Folei [1 ]
Huang, Lanxi [1 ]
Wang, Maolin [1 ]
Wang, Yue [1 ]
Chen, Xiaochuan [1 ]
机构：
[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China
来源：
TETRAHEDRON LETTERS | 2024年 / 142卷
基金：
中国国家自然科学基金;
关键词：
Epoxyquinone; Anhydrogabosine; Epoxydon; Epofomin; Natural product synthesis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ENDOPHYTIC FUNGUS; EFFICIENT SYNTHESIS; SECONDARY METABOLITES; BIOLOGICAL-ACTIVITY; NATURAL-PRODUCTS; (+)-EPIEPOXYDON; INHIBITORS; (+)-EPIEPOFORMIN; (+)-BROMOXONE;
D O I：
10.1016/j.tetlet.2024.155082
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A collective synthesis of the C7 epoxyquinones has been achieved by a concise and flexible strategy, in which the employment of (-)-shikimic acid as starting material permits the rapid preparation of the polyhydroxylated bromocyclohexene intermediate. (-)-Parasitenone, (+)-epoxydon and its monoactate, (-)-phyllostine and its acetate were readily synthesized via the oxirane ring closure of bromohydrin precursors. Moreover, the key intermediate was successfully extended for the synthesis of the epoxyquinones with a methyl group including (+)-epoformin, (+)-epiepoformin and (-)-theobroxide by sulfonate reduction method for the first time.
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页数：4
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