Literature DB >> 27037993

Asymmetric Synthesis of Axinellamines A and B.

Zhiqiang Ma1, Xiao Wang1,2, Yuyong Ma1,2, Chuo Chen3.   

Abstract

Axinellamines A and B are broad-spectrum antibacterial pyrrole-imidazole alkaloids that have a complex polycyclic skeleton. A new asymmetric synthesis of these marine sponge metabolites is described herein, featuring an oxidative rearrangement and an anchimeric chlorination reaction.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; anchimeric assistance; axinellamines; natural products; total synthesis

Mesh：

Substances：

Year:  2016        PMID： 27037993      PMCID： PMC4836294          DOI： 10.1002/anie.201600007

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  41 in total

1.  Total synthesis of (+/-)-axinellamines A and B.

Authors:  Daniel P O'Malley; Junichiro Yamaguchi; Ian S Young; Ian B Seiple; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate.

Authors:  Manuel A Zancanella; Daniel Romo
Journal:  Org Lett       Date:  2008-08-12       Impact factor: 6.005

3.  Stable 5-substituted cyclopentadienes for the Diels-Alder cycloaddition and their application to the synthesis of palau'amine.

Authors:  Jonathan Hudon; Timothy A Cernak; James A Ashenhurst; James L Gleason
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Regiocontrol in Mn(III)-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers.

Authors:  Xianghui Tan; Chuo Chen
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-26       Impact factor: 15.336

5.  Synthetic (±)-axinellamines deficient in halogen.

Authors:  Hui Ding; Andrew G Roberts; Patrick G Harran
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-19       Impact factor: 15.336

6.  Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Authors:  Ian B Seiple; Shun Su; Ian S Young; Akifumi Nakamura; Junichiro Yamaguchi; Lars Jørgensen; Rodrigo A Rodriguez; Daniel P O'Malley; Tanja Gaich; Matthias Köck; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-08-23       Impact factor: 15.419

Review 7.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors:  Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal:  Nat Prod Rep       Date:  2011-05-09       Impact factor: 13.423

8.  Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine.

Authors:  Zhiqiang Ma; Jianming Lu; Xiao Wang; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2010-09-16       Impact factor: 6.222

9.  Synthesis of the Carbocyclic Core of Massadine.

Authors:  Chunrui Sun; Hyunjin Lee; Daesung Lee
Journal:  Org Lett       Date:  2015-10-26       Impact factor: 6.005

10.  Oxidative rearrangement of imidazoles with dimethyldioxirane.

Authors:  Carl J Lovely; Hongwang Du; Yong He; H V Rasika Dias
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005
View more
  5 in total

1.  Rapid access to the core skeleton of the [3 + 2]-type dimeric pyrrole-imidazole alkaloids by triplet ketone-mediated C-H functionalization.

Authors:  Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-12-15       Impact factor: 2.457

2.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

3.  Iron-Catalyzed Direct Olefin Diazidation via Peroxyester Activation Promoted by Nitrogen-Based Ligands.

Authors:  Shou-Jie Shen; Cheng-Liang Zhu; Deng-Fu Lu; Hao Xu
Journal:  ACS Catal       Date:  2018-04-06       Impact factor: 13.084

4.  Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter.

Authors:  Zhiqiang Ma; Lin You; Chuo Chen
Journal:  J Org Chem       Date:  2016-12-20       Impact factor: 4.354

5.  One-Step Synthesis of 2,5-Diaminoimidazoles and Total Synthesis of Methylglyoxal-Derived Imidazolium Crosslink (MODIC).

Authors:  Venkata R Sabbasani; Kung-Pern Wang; Matthew D Streeter; David A Spiegel
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-12       Impact factor: 15.336
  5 in total

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