Literature DB >> 30721058

Asymmetric Total Synthesis of Cerorubenic Acid-III.

Xin Liu1,2, Junyang Liu1,3, Jianlei Wu1, Guocheng Huang1, Rong Liang1, Lung Wa Chung1, Chuang-Chuang Li1.   

Abstract

The first asymmetric total synthesis of the highly strained compound cerorubenic acid-III is reported. A type II intramolecular [5 + 2] cycloaddition allowed efficient and diastereoselective construction of the synthetically challenging bicyclo[4.4.1] ring system with a strained bridgehead (anti-Bredt) double bond in the final product. A unique transannular cyclization installed the vinylcyclopropane moiety with retention of the desired stereochemistry.

Entities:  

Year:  2019        PMID： 30721058     DOI： 10.1021/jacs.8b12647

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


  5 in total

1.  Maltol- and Allomaltol-Derived Oxidopyrylium Ylides: Methyl Substitution Pattern Kinetically Influences [5 + 3] Dimerization versus [5 + 2] Cycloaddition Reactions.

Authors:  Lauren P Bejcek; Aswin K Garimallaprabhakaran; Duygu M Suyabatmaz; Alexander Greer; William H Hersh; Edyta M Greer; Ryan P Murelli
Journal:  J Org Chem       Date:  2019-10-25       Impact factor: 4.354

2.  Synthesis of aryl-substituted 2-methoxyphenol derivatives from maltol-derived oxidopyrylium cycloadducts through an acid-mediated ring contraction cascade.

Authors:  Lauren P Bejcek; Ryan P Murelli
Journal:  Chem Commun (Camb)       Date:  2020-02-18       Impact factor: 6.222

3.  Investigations into a Stoichiometrically Equivalent Intermolecular Oxidopyrylium [5 + 2] Cycloaddition Reaction Leveraging 3-Hydroxy-4-pyrone-Based Oxidopyrylium Dimers.

Authors:  Daniel V Schiavone; Diana M Kapkayeva; Ryan P Murelli
Journal:  J Org Chem       Date:  2021-02-15       Impact factor: 4.354

4.  Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition.

Authors:  Jianyu Zhang; Xi Wang; Tao Xu
Journal:  Nat Commun       Date:  2021-05-21       Impact factor: 14.919

Review 5.  Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes.

Authors:  Emmanuelle Lautié; Olivier Russo; Pierre Ducrot; Jean A Boutin
Journal:  Front Pharmacol       Date:  2020-04-07       Impact factor: 5.810
  5 in total

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