Literature DB >> 20098427

Domino access to highly substituted chromans and isochromans from carbohydrates.

Markus Leibeling1, Dennis C Koester, Martin Pawliczek, Svenia C Schild, Daniel B Werz.   

Abstract

Herein we describe the synthesis of highly substituted chromans and isochromans using carbohydrates as starting materials. Our approach makes use of a Pd-catalyzed domino reaction consisting of oxidative addition, followed by two carbopalladation steps and completed by a cyclization to annelate the benzene moiety. The versatility of this route has been demonstrated by a small library of highly substituted chromans and isochromans.

Entities:  

Year:  2010        PMID: 20098427     DOI: 10.1038/nchembio.302

Source DB:  PubMed          Journal:  Nat Chem Biol        ISSN: 1552-4450            Impact factor:   15.040


  16 in total

1.  Domino Reactions in Organic Synthesis.

Authors:  Lutz F. Tietze
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Control of four stereocentres in a triple cascade organocatalytic reaction.

Authors:  Dieter Enders; Matthias R M Hüttl; Christoph Grondal; Gerhard Raabe
Journal:  Nature       Date:  2006-06-15       Impact factor: 49.962

3.  Catalytic asymmetric oxa-Michael-Michael cascade for facile construction of chiral chromans via an aminal intermediate.

Authors:  Liansuo Zu; Shilei Zhang; Hexin Xie; Wei Wang
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

4.  Synthesis of indoles via domino reaction of N-aryl amides and ethyl diazoacetate.

Authors:  Sun-Liang Cui; Jing Wang; Yan-Guang Wang
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

5.  Organocatalytic asymmetric Friedel-Crafts alkylation/cyclization cascade reaction of 1-naphthols and alpha,beta-unsaturated aldehydes: an enantioselective synthesis of chromanes and dihydrobenzopyranes.

Authors:  Liang Hong; Lei Wang; Wangsheng Sun; Kwokyin Wong; Rui Wang
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

6.  A new pd-catalyzed cascade reaction for the synthesis of strained aromatic polycycles.

Authors:  Gaëlle Blond; Christophe Bour; Bahaâ Salem; Jean Suffert
Journal:  Org Lett       Date:  2008-02-15       Impact factor: 6.005

7.  Gold-catalyzed synthesis of chroman, dihydrobenzofuran, dihydroindole, and tetrahydroquinoline derivatives.

Authors:  A Stephen K Hashmi; Matthias Rudolph; Jan W Bats; Wolfgang Frey; Frank Rominger; Thomas Oeser
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

8.  Synthesis of chromans via [3 + 3] cyclocoupling of phenols with allylic alcohols using a Mo/o-chloranil catalyst system.

Authors:  Yoshihiko Yamamoto; Kouhei Itonaga
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

9.  Ruthenium-catalyzed enantioselective carbon-carbon bond forming reaction via allenylidene-ene process: synthetic approach to chiral heterocycles such as chromane, thiochromane, and 1,2,3,4-tetrahydroquinoline derivatives.

Authors:  Koji Fukamizu; Yoshihiro Miyake; Yoshiaki Nishibayashi
Journal:  J Am Chem Soc       Date:  2008-07-22       Impact factor: 15.419

10.  PPh3-catalyzed domino reaction: a facile method for the synthesis of chroman derivatives.

Authors:  Xiangtai Meng; You Huang; Hongxia Zhao; Peizhong Xie; Jianze Ma; Ruyu Chen
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

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  13 in total

1.  Celebrating synthesis.

Authors: 
Journal:  Nat Chem Biol       Date:  2011-11-15       Impact factor: 15.040

2.  Synthetic chemistry: An upfront investment.

Authors:  Damian W Young
Journal:  Nat Chem Biol       Date:  2010-03       Impact factor: 15.040

3.  Synthesis of chromans via Pd-catalyzed alkene carboetherification reactions.

Authors:  Amanda F Ward; Yan Xu; John P Wolfe
Journal:  Chem Commun (Camb)       Date:  2011-11-24       Impact factor: 6.222

4.  Synthesis and Structural Characterization of 1-(E-1-Arylpropenon-3-yl)-3,4,6-tri-O-benzyl-d-glucals and Their Transformation into Pentasubstituted (2R,3S,4R)-Chromanes via Pd-Catalyzed Cross Dehydrogenative Coupling Reaction.

Authors:  Bhawani Shankar; Vinod Khatri; Banty Kumar; Vipin K Maikhuri; Amit Kumar; Rashmi Tomar; Ashok K Prasad
Journal:  ACS Omega       Date:  2021-04-22

5.  Sonogashira-Hagihara reactions of halogenated glycals.

Authors:  Dennis C Koester; Daniel B Werz
Journal:  Beilstein J Org Chem       Date:  2012-05-02       Impact factor: 2.883

6.  Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions.

Authors:  Markus Leibeling; Daniel B Werz
Journal:  Beilstein J Org Chem       Date:  2013-10-24       Impact factor: 2.883

7.  Benzene construction via Pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes.

Authors:  Yuchen Zhang; Wangteng Wu; Chunling Fu; Xin Huang; Shengming Ma
Journal:  Chem Sci       Date:  2018-12-19       Impact factor: 9.825

8.  Total Synthesis of (+)-Rubriflordilactone A.

Authors:  Shermin S Goh; Guilhem Chaubet; Birgit Gockel; Marie-Caroline A Cordonnier; Hannah Baars; Andrew W Phillips; Edward A Anderson
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-04       Impact factor: 15.336

9.  Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A.

Authors:  Guilhem Chaubet; Shermin S Goh; Mujahid Mohammad; Birgit Gockel; Marie-Caroline A Cordonnier; Hannah Baars; Andrew W Phillips; Edward A Anderson
Journal:  Chemistry       Date:  2017-09-08       Impact factor: 5.236

10.  Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core.

Authors:  Fatima Zahra Bamou; Tam Minh Le; Bettina Volford; András Szekeres; Zsolt Szakonyi
Journal:  Molecules       Date:  2019-12-19       Impact factor: 4.411

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