Literature DB >> 29711622

Investigations into the Manzamine Alkaloid Biosynthetic Hypothesis.

Jack E Baldwin1, Timothy D W Claridge1, Andrew J Culshaw1, Florian A Heupel1, Victor Lee1, David R Spring1, Roger C Whitehead1, Robert J Boughtflower2, Ian M Mutton2, Richard J Upton2.   

Abstract

The biomimetic synthesis of a pentacyclic alkaloid (keramaphidin B, 1), an intermediate in the biogenetic pathway to the manzamine alkaloids, has been achieved. Compound 1 was formed by an intramolecular Diels-Alder reaction of macrocycle 2 in buffer followed by reduction with NaBH4 . This reaction provides the first direct expeimental evidence for the authors' biosynthetic hypothesis. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Alkaloids; Biomimetic synthesis; Biosynthesis; Diels-Alder reactions; Manzamine

Year:  1998        PMID: 29711622     DOI: 10.1002/(SICI)1521-3773(19981016)37:19<2661::AID-ANIE2661>3.0.CO;2-D

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


  5 in total

Review 1.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

2.  A Unified Approach to Polycyclic Alkaloids of the Ingenamine Estate: Total Syntheses of Keramaphidin B, Ingenamine, and Nominal Njaoamine I.

Authors:  Zhanchao Meng; Simon M Spohr; Sandra Tobegen; Christophe Farès; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2021-08-27       Impact factor: 15.419

3.  Neopetrocyclamines A and B, polycyclic diamine alkaloids from the sponge Neopetrosia cf exigua.

Authors:  Zhibin Liang; Florian J Sulzmaier; Wesley Y Yoshida; Michelle Kelly; Joe W Ramos; Philip G Williams
Journal:  J Nat Prod       Date:  2015-01-13       Impact factor: 4.803

4.  Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation.

Authors:  Joseph B Sweeney; Julien Doulcet; Bimod Thapa
Journal:  iScience       Date:  2018-11-01

5.  Total Synthesis Provides Strong Evidence: Xestocyclamine A is the Enantiomer of Ingenamine.

Authors:  Zhanchao Meng; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2020-06-23       Impact factor: 15.419

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.