Literature DB >> 23956022

Total synthesis and structural revision of laurefurenynes A and B.

Michael T Holmes1, Robert Britton.   

Abstract

Structural reassignment: A total synthesis of the proposed structure of (-)-laurefurenyne A has been accomplished that relies on organocatalytic aldehyde α-chlorination and a flexible chlorohydrin-based strategy for stereocontrolled access to the bis-tetrahydrofuran core of the natural product. Analysis of incongruities between the (1) H NMR spectra of synthetic and natural material led to a configurational reassignment for the natural product, which was also confirmed by total synthesis.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  chlorohydrin; laurefurenyne A; laurencia acetogenins; organocatalysis; total synthesis

Mesh:

Substances:

Year:  2013        PMID: 23956022     DOI: 10.1002/chem.201302352

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


  6 in total

1.  A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K.

Authors:  Sharon E Michalak; Sangkil Nam; David M Kwon; David A Horne; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2019-06-03       Impact factor: 15.419

Review 2.  Stereoselective Halogenation in Natural Product Synthesis.

Authors:  Won-jin Chung; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

3.  Stereochemical determination of five-membered cyclic ether acetogenins using a spin-spin coupling constant approach and DFT calculations.

Authors:  Adrián Gutiérrez-Cepeda; Antonio Hernández Daranas; José J Fernández; Manuel Norte; María L Souto
Journal:  Mar Drugs       Date:  2014-07-01       Impact factor: 5.118

4.  Structure Determination of a Chloroenyne from Laurencia majuscula Using Computational Methods and Total Synthesis.

Authors:  Erin D Shepherd; Bryony S Dyson; William E Hak; Quynh Nhu N Nguyen; Miseon Lee; Mi Jung Kim; Te-Ik Sohn; Deukjoon Kim; Jonathan W Burton; Robert S Paton
Journal:  J Org Chem       Date:  2019-04-12       Impact factor: 4.354

5.  Forwards and backwards - synthesis of Laurencia natural products using a biomimetic and retrobiomimetic strategy incorporating structural reassignment of laurefurenynes C-F.

Authors:  Hau Sun Sam Chan; Amber L Thompson; Kirsten E Christensen; Jonathan W Burton
Journal:  Chem Sci       Date:  2020-10-08       Impact factor: 9.825

6.  Structure reassignment of laurefurenynes A and B by computation and total synthesis.

Authors:  David J Shepherd; Phillip A Broadwith; Bryony S Dyson; Robert S Paton; Jonathan W Burton
Journal:  Chemistry       Date:  2013-08-21       Impact factor: 5.236

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.