Literature DB >> 26146420

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

Michael T Taylor1, Joseph M Fox1.   

Abstract

An electrophilic bromine catalyzed skeletal rearrangement of an Δ4-oxocene to an epoxy furan has been described. This skeletal rearrangement suggests a plausible mechanism for the biosynthesis of the C15-acetogenin laurepoxide.

Entities:  

Keywords:  biosynthesis; laurepoxide; rearrangement; Δ4-oxocene epoxide

Year:  2015        PMID： 26146420      PMCID： PMC4489422          DOI： 10.1016/j.tetlet.2015.03.009

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  11 in total

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Review 2.  Marine natural products.

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Review 3.  Marine natural products.

Authors:  D J Faulkner
Journal:  Nat Prod Rep       Date:  1998-04       Impact factor: 13.423

4.  Proof-of-principle direct double cyclisation of a linear C15-precursor to a dibrominated bicyclic medium-ring ether relevant to Laurencia species.

Authors:  D Christopher Braddock; Dan-Tiberiu Sbircea
Journal:  Chem Commun (Camb)       Date:  2014-10-28       Impact factor: 6.222

5.  Concise synthetic approaches for the Laurencia family: formal total syntheses of (±)-laurefucin and (±)-E- and (±)-Z-pinnatifidenyne.

Authors:  Scott A Snyder; Alexandria P Brucks; Daniel S Treitler; Ioana Moga
Journal:  J Am Chem Soc       Date:  2012-10-11       Impact factor: 15.419

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

Authors:  Scott A Snyder; Daniel S Treitler; Alexandria P Brucks; Wesley Sattler
Journal:  J Am Chem Soc       Date:  2011-09-16       Impact factor: 15.419

7.  Intramolecular bromonium ion assisted epoxide ring-opening: capture of the oxonium ion with an added external nucleophile.

Authors:  Karl J Bonney; D Christopher Braddock; Andrew J P White; Muhammad Yaqoob
Journal:  J Org Chem       Date:  2010-11-29       Impact factor: 4.354

8.  Total synthesis and structure confirmation of elatenyne: success of computational methods for NMR prediction with highly flexible diastereomers.

Authors:  Bryony S Dyson; Jonathan W Burton; Te-ik Sohn; Byungsook Kim; Hoon Bae; Deukjoon Kim
Journal:  J Am Chem Soc       Date:  2012-07-03       Impact factor: 15.419

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

Authors:  Byungsook Kim; Miseon Lee; Mi Jung Kim; Hyunjoo Lee; Sanghee Kim; Deukjoon Kim; Minseob Koh; Seung Bum Park; Kye Jung Shin
Journal:  J Am Chem Soc       Date:  2008-12-10       Impact factor: 15.419

10.  Toward a formal synthesis of laureatin: unexpected rearrangements involving cyclic ether nucleophiles.

Authors:  Santosh Keshipeddy; Isamir Martínez; Bernard F Castillo; Martha D Morton; Amy R Howell
Journal:  J Org Chem       Date:  2012-09-05       Impact factor: 4.354
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  3 in total

1.  Dual-Reactivity trans-Cyclooctenol Probes for Sulfenylation in Live Cells Enable Temporal Control via Bioorthogonal Quenching.

Authors:  Samuel L Scinto; Oshini Ekanayake; Uthpala Seneviratne; Jessica E Pigga; Samantha J Boyd; Michael T Taylor; Jun Liu; Christopher W Am Ende; Sharon Rozovsky; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2019-07-09       Impact factor: 15.419

2.  Computationally guided discovery of a reactive, hydrophilic trans-5-oxocene dienophile for bioorthogonal labeling.

Authors:  William D Lambert; Samuel L Scinto; Olga Dmitrenko; Samantha J Boyd; Ronald Magboo; Ryan A Mehl; Jason W Chin; Joseph M Fox; Stephen Wallace
Journal:  Org Biomol Chem       Date:  2017-08-09       Impact factor: 3.876

3.  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
  3 in total

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