Literature DB >> 17508363

Total synthesis of five thapsigargins: guaianolide natural products exhibiting sub-nanomolar SERCA inhibition.

Stephen P Andrews1, Matthew Ball, Frank Wierschem, Ed Cleator, Steven Oliver, Klemens Högenauer, Oliver Simic, Alessandra Antonello, Udo Hünger, Martin D Smith, Steven V Ley.   

Abstract

Herein we describe the total synthesis of five guaianolide natural products: thapsigargin, thapsivillosin C, thapsivillosin F, trilobolide and nortrilobolide. Prodrug derivatives of thapsigargin have shown selective in vivo cytotoxicity against prostate tumours and the need for further investigation of this phenomenon highlights the importance of these total syntheses. The first absolute stereochemical assignment of thapsivillosin C is also delineated.

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17508363     DOI： 10.1002/chem.200700302

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  15 in total

1.  An allenic Pauson-Khand approach to 6,12-guaianolides.

Authors:  Francois Grillet; Chaofeng Huang; Kay M Brummond
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

2.  Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene-Imine [3 + 2] Annulation.

Authors:  Andrew J Smaligo; Sriramurthy Vardhineedi; Ohyun Kwon
Journal:  ACS Catal       Date:  2018-05-04       Impact factor: 13.084

3.  Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.

Authors:  Xirui Hu; Andrew J Musacchio; Xingyu Shen; Yujia Tao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

4.  Localization and in-Vivo Characterization of Thapsia garganica CYP76AE2 Indicates a Role in Thapsigargin Biosynthesis.

Authors:  Trine Bundgaard Andersen; Karen Agatha Martinez-Swatson; Silas Anselm Rasmussen; Berin Alain Boughton; Kirsten Jørgensen; Johan Andersen-Ranberg; Nils Nyberg; Søren Brøgger Christensen; Henrik Toft Simonsen
Journal:  Plant Physiol       Date:  2017-03-08       Impact factor: 8.340

5.  A Double Allylation Strategy for Gram-Scale Guaianolide Production: Total Synthesis of (+)-Mikanokryptin.

Authors:  Xirui Hu; Silong Xu; Thomas J Maimone
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-03       Impact factor: 15.336

6.  Function-Oriented and Modular (+/-)-cis-Pseudoguaianolide Synthesis: Discovery of New Nrf2 Activators and NF-κB Inhibitors.

Authors:  Fabien Emmetiere; Ranjala Ratnayake; Henry A M Schares; Katherine F M Jones; Emily Bevan-Smith; Hendrik Luesch; Daniel A Harki; Alexander J Grenning
Journal:  Chemistry       Date:  2021-02-26       Impact factor: 5.236

7.  From Plant to Patient: Thapsigargin, a Tool for Understanding Natural Product Chemistry, Total Syntheses, Biosynthesis, Taxonomy, ATPases, Cell Death, and Drug Development.

Authors:  Søren Brøgger Christensen; Henrik Toft Simonsen; Nikolai Engedal; Poul Nissen; Jesper Vuust Møller; Samuel R Denmeade; John T Isaacs
Journal:  Prog Chem Org Nat Prod       Date:  2021

8.  A redox economical synthesis of bioactive 6,12-guaianolides.

Authors:  Bo Wen; Joseph K Hexum; John C Widen; Daniel A Harki; Kay M Brummond
Journal:  Org Lett       Date:  2013-05-10       Impact factor: 6.005

Review 9.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

10.  Oro-gustatory perception of dietary lipids and calcium signaling in taste bud cells are altered in nutritionally obesity-prone Psammomys obesus.

Authors:  Souleymane Abdoul-Azize; Feriel Atek-Mebarki; Arezki Bitam; Hassimi Sadou; Elhadj Ahmed Koceïr; Naim Akhtar Khan
Journal:  PLoS One       Date:  2013-08-01       Impact factor: 3.240
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.