Asymmetric Total Synthesis of the Naturally Occurring Antibiotic Anthracimycin.,Organic Letters

当前位置： X-MOL 学术 › Org. Lett. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Asymmetric Total Synthesis of the Naturally Occurring Antibiotic Anthracimycin.
Organic Letters ( IF 4.9 ) Pub Date : 2020-06-29 , DOI: 10.1021/acs.orglett.0c01913
Emma K Davison _{1,

2,

3} , Jared L Freeman _{1,

3} , Wanli Zhang ₄ , William M Wuest _{4,

5} , Daniel P Furkert _{1,

3} , Margaret A Brimble _{1,

2,

3}

Affiliation

The first total synthesis of the potent antibiotic anthracimycin was achieved in 20 steps. The synthesis features an intramolecular Diels–Alder reaction to forge the trans-decalin moiety, and an unprecedented aldol reaction using a complex β-ketoester to provide the tricarbonyl motif. A Stork–Zhao olefination and Grubbs ring closing metathesis delivered the E/Z-diene and forged the macrocycle. The C2 configuration was set with a base-mediated epimerization, providing access to (−)-anthracimycin.

中文翻译：

天然抗生素蒽霉素的不对称全合成。

强效抗生素蒽霉素的首次全合成经过 20 个步骤实现。该合成的特点是通过分子内狄尔斯-阿尔德反应形成反式十氢化萘部分，以及使用复杂的β-酮酯来提供三羰基基序的前所未有的羟醛反应。Stork-Zhao 烯化和 Grubbs 闭环复分解产生了E / Z -二烯并形成了大环。C2构型通过碱基介导的差向异构化设置，从而提供对(-)-蒽霉素的接触。

更新日期：2020-07-17

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南