Literature DB >> 19049472

Biomimetic asymmetric total synthesis of (-)-laurefucin via an organoselenium-mediated intramolecular hydroxyetherification.

Byungsook Kim1, Miseon Lee, Mi Jung Kim, Hyunjoo Lee, Sanghee Kim, Deukjoon Kim, Minseob Koh, Seung Bum Park, Kye Jung Shin.   

Abstract

The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.

Entities:  

Mesh:

Substances:

Year:  2008        PMID: 19049472     DOI: 10.1021/ja806304s

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  6 in total

1.  Biosynthesis of the C15-acetogenin laurepoxide may involve bromine-induced skeletal rearrangement of a Δ4-oxocene precursor.

Authors:  Michael T Taylor; Joseph M Fox
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

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.  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

4.  Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin.

Authors:  Victoria Sinka; Daniel A Cruz; Víctor S Martín; Juan I Padrón
Journal:  Org Lett       Date:  2022-07-14       Impact factor: 6.072

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.