Literature DB >> 35846850

A Ring Expansion Approach To N-oxy-2,5-diketopiperazines.

Amy C Jackson1, James T Olsen1, Sasha Sundstrom1, Kyle M Lambert1, John L Wood1.   

Abstract

A ring expansion of tetramic acids (pyrrolidine-2,4-diones) to N-oxy-2,5-diketopiperazines (DKPs) is described. This method allows for the facile and late-stage construction of the hydroxamic acid moiety and can thereby serve as a general method for accessing N-oxy-2,5-DKP natural products.

Entities:  

Year:  2022        PMID： 35846850      PMCID： PMC9281442          DOI： 10.1016/j.tetlet.2022.153851

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.032


  16 in total

Review 1.  2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products.

Authors:  Alan D Borthwick
Journal:  Chem Rev       Date:  2012-05-11       Impact factor: 60.622

2.  Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds.

Authors:  Kyle M Lambert; Joshua B Cox; Lin Liu; Amy C Jackson; Sam Yruegas; Kenneth B Wiberg; John L Wood
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-08       Impact factor: 15.336

3.  Efficient solid-phase synthesis of highly functionalized 1,4-benzodiazepin-5-one derivatives and related compounds by intramolecular aza-Wittig reactions.

Authors:  Carmen Gil; Stefan Bräse
Journal:  Chemistry       Date:  2005-04-22       Impact factor: 5.236

4.  Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.

Authors:  Xia Tian; Juan Feng; Shi-Ming Fan; Xiao-Li Zhen; Jian-Rong Han; Shou-Xin Liu
Journal:  Bioorg Med Chem       Date:  2016-08-24       Impact factor: 3.641

Review 5.  Diketopiperazines from marine organisms.

Authors:  Riming Huang; Xuefeng Zhou; Tunhai Xu; Xianwen Yang; Yonghong Liu
Journal:  Chem Biodivers       Date:  2010-12       Impact factor: 2.408

6.  Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

Authors:  David W Lin; Takeshi Masuda; Moritz B Biskup; Jonathan D Nelson; Phil S Baran
Journal:  J Org Chem       Date:  2011-01-20       Impact factor: 4.354

7.  Penicisulfuranols A-F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309.

Authors:  Meilin Zhu; Xiaomin Zhang; Huimin Feng; Jiajia Dai; Jing Li; Qian Che; Qianqun Gu; Tianjiao Zhu; Dehai Li
Journal:  J Nat Prod       Date:  2016-12-19       Impact factor: 4.050

8.  Raistrickindole A, an Anti-HCV Oxazinoindole Alkaloid from Penicillium raistrickii IMB17-034.

Authors:  Jiao Li; Yuanyuan Hu; Xiaomeng Hao; Jiali Tan; Fang Li; Xinran Qiao; Shuzhen Chen; Chunling Xiao; Minghua Chen; Zonggen Peng; Maoluo Gan
Journal:  J Nat Prod       Date:  2019-04-23       Impact factor: 4.050

9.  Haenamindole, an unusual diketopiperazine derivative from a marine-derived Penicillium sp. KCB12F005.

Authors:  Jong Won Kim; Sung-Kyun Ko; Sangkeun Son; Kee-Sun Shin; In-Ja Ryoo; Young-Soo Hong; Hyuncheol Oh; Bang Yeon Hwang; Hiroshi Hirota; Shunji Takahashi; Bo Yeon Kim; Hiroyuki Osada; Jae-Hyuk Jang; Jong Seog Ahn
Journal:  Bioorg Med Chem Lett       Date:  2015-09-10       Impact factor: 2.823

10.  Synthesis of cyclic hydroxamic acids through -NOH insertion of ketones.

Authors:  Ranjan Banerjee; S Bruce King
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005
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