Total Synthesis of Diverse Tetramic Acid Bearing cis-Decalin Natural Products

被引：9

作者：

Dong, Haoran ^{[1
]}

Hu, Dachao ^{[2
]}

Hong, Benke ^{[1
]}

Wang, Jin ^{[1
]}

Lei, Xiaoguang ^{[1
,3
]}

机构：

[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, State Key Lab Nat & Biomimet Drugs, Dept Chem Biol,Synthet & Funct Biomol Ctr,Coll Che, Beijing 100871, Peoples R China

[2] Peking Univ, Peking Univ Tsinghua Univ Natl Inst Biol Sci Joint, Sch Life Sci, Beijing 100871, Peoples R China

[3] Peking Univ, Acad Adv Interdisciplinary Studies, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 20期

基金：

中国国家自然科学基金;

关键词：

Cis-Decalin; Epoxidation; Intramolecular Diels-Alder Reaction; Natural Products; Total Synthesis; INTRAMOLECULAR DIELS-ALDER; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; SYMMETRIC DIENE ACETALS; DOUBLE IODOETHERIFICATION; TRANSITION-STATES; CYCLOADDITION; INVOLVEMENT; EPOXIDATION; CENTERS;

D O I：

10.1002/anie.202301872

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report herein the first total syntheses of four natural antibiotics, vermisporin, PF1052/AB4015-A, AB4015-L, AB4015-B, and one hydrogenated natural product derivative, AB4015-A2, that all feature a tetramic acid bearing cis-decalin ring. The construction of the functionalized cis-decalin ring was achieved by a diastereoselective intramolecular Diels-Alder (IMDA) reaction, which proceeded via a rare endo-boat transition state. Through an intramolecular neighboring-group-oriented strategy, the sterically hindered epoxy group in vermisporin, PF1052/AB4015-A and AB4015-L was installed efficiently. A one-pot aminolysis/Dieckmann condensation cascade using l-amino acid derivatives afforded the desired tetramic acid structure. The total synthesis led to the unambiguous verification of the absolute configuration of these natural products.

引用

页数：6

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