Total synthesis of angelone enabled by a remarkable biomimetic sequence

被引：26

作者：

Tan, Haibo ^{[1
]}

Chen, Xinzheng ^{[1
]}

Liu, Zheng ^{[1
]}

Wang, David Zhigang ^{[1
]}

机构：

[1] Shenzhen Univ Town, Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol,Key Lab Chem Genom, Shenzhen 518055, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 21期

基金：

美国国家科学基金会;

关键词：

Singlet oxygen; Diels-Alder Reaction; Electrocyclization; Kornblum-DeLaMare Rearrangement; Biomimetic synthesis; INDOLE ALKALOIDS; NAUCLEA-OFFICINALIS; EPOXYQUINOL-A; REACTIVITY;

D O I：

10.1016/j.tet.2012.03.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The natural product angelone was readily accessed with a remarkable biomimetic journey that sequentially features carbonyl formation elimination, 6 pi-electrocyclization, visible light-promoted singlet O-2 Diels-Alder reaction, Kornblum-DeLaMare-type peroxide rearrangement, 6 pi-electrocyclic ring-opening, and conjugative addition-elimination as the key steps. With key intermediates isolated and characterized, this study stands to reveal a rare system in which bio-inspired synthetic strategies were found to mirror experimental realities. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3952 / 3955

页数：4

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