Literature DB >> 21919540

A general strategy for the stereocontrolled preparation of diverse 8- and 9-membered Laurencia-type bromoethers.

Scott A Snyder1, Daniel S Treitler, Alexandria P Brucks, Wesley Sattler.   

Abstract

A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8- and 9-membered bromoethers in a regio- and stereocontrolled manner through the use of BDSB (bromodiethylsulfonium bromopentachloroantimonate). These products resemble the cores of the Laurencia C15 acetogenins. In light of the generality and effectiveness of the approach, this work provides a unique strategy for their laboratory preparation and may implicate a possible biosynthesis pathway.

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Year:  2011        PMID: 21919540     DOI: 10.1021/ja2069449

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


  8 in total

1.  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

2.  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

3.  Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation.

Authors:  Megan L Lanier; Hyeri Park; Paramita Mukherjee; Jacob C Timmerman; Anthony A Ribeiro; Ross A Widenhoefer; Jiyong Hong
Journal:  Chemistry       Date:  2017-05-03       Impact factor: 5.236

4.  Enantiospecific Solvolytic Functionalization of Bromochlorides.

Authors:  Alexander J Burckle; Bálint Gál; Frederick J Seidl; Vasil H Vasilev; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2017-09-18       Impact factor: 15.419

Review 5.  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

6.  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

7.  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

8.  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

  8 in total

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