Total Synthesis of the 2,5-Disubstituted γ-Pyrone E1 UAE Inhibitor Himeic Acid A

被引：3

作者：

Lu, Heyuan ^{[1
]}

Handore, Kishor L. ^{[1
]}

Wood, Tabitha E. ^{[1
,2
]}

Shimokura, Grace K. ^{[1
]}

Schimmer, Aaron D. ^{[2
]}

Batey, Robert A. ^{[1
,3
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

[2] Univ Hlth Network, Princess Margaret Canc Ctr, Toronto, ON M5G 1L7, Canada

[3] Univ Toronto, Accelerat Consortium, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 41期

基金：

加拿大自然科学与工程研究理事会;

关键词：

UBIQUITIN-ACTIVATING ENZYME; MARINE-DERIVED FUNGUS; 4-PYRIDONE DERIVATIVES; METABOLITES;

D O I：

10.1021/acs.orglett.3c02761

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the E1 ubiquitin-activating enzyme inhibitor, himeic acid A, is reported. A McCombie reaction was used to form the core gamma-pyrone via a 6 pi-electrocyclization. A dioxenone ring-opening/acyl ketene trapping reaction with a primary amide provided the unusual unsymmetrical imide functionality. Other key steps include the use of an Evans auxiliary alkylation (d.r. >= 95:5) to install the (S)-2-methyl succinic acid fragment and a cross-metathesis to install the unsaturated side-chain.

引用

页码：7502 / 7506

页数：5

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