Literature DB >> 20078081

Enantioselective total synthesis of (+)-conicol via cascade three-component organocatalysis.

Bor-Cherng Hong1, Prakash Kotame, Chih-Wei Tsai, Ju-Hsiou Liao.   

Abstract

The first asymmetric total synthesis of (+)-conicol has been achieved via a key step reaction involving the organocatalytic domino oxa-Michael-Michael-Michael-aldol condensation of 2-((E)-2-nitrovinyl)benzene-1,4-diol and alpha,beta-unsaturated aldehydes. Structures of the three-component domino reaction adducts, 20 and 21, including their absolute configurations, were confirmed unambiguously by X-ray analysis. Through this work, the absolute configuration of (+)-conicol was thereby elucidated.

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Year:  2010        PMID: 20078081     DOI: 10.1021/ol902840x

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  12 in total

1.  Synthesis of Oxazolidinone and Tosyl Enamines by Tertiary Amine Catalysis.

Authors:  Nicholas A Eddy; Peter D Morse; Martha D Morton; Gabriel Fenteany
Journal:  Synlett       Date:  2011-01-01       Impact factor: 2.454

Review 2.  Recent advances in C-heteroatom bond forming by asymmetric Michael addition.

Authors:  Majid M Heravi; Parvin Hajiabbasi
Journal:  Mol Divers       Date:  2013-12-31       Impact factor: 2.943

3.  Diastereodivergent Synthesis of Hexahydro-6H-benzo[c]chromen-6-one Derivatives Catalyzed by Modularly Designed Organocatalysts.

Authors:  Satish Jakkampudi; Ramarao Parella; Hadi D Arman; John C-G Zhao
Journal:  Chemistry       Date:  2019-05-09       Impact factor: 5.236

4.  An organocascade kinetic resolution.

Authors:  Patrick G McGarraugh; Stacey E Brenner-Moyer
Journal:  Org Lett       Date:  2011-11-15       Impact factor: 6.005

5.  Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts.

Authors:  Satish Jakkampudi; Ramarao Parella; John C-G Zhao
Journal:  Org Biomol Chem       Date:  2018-12-19       Impact factor: 3.876

6.  An Asymmetric Organocatalytic Quadruple Cascade to Tetraaryl-Substituted 2-Azabicyclo[3.3.0]octadienones.

Authors:  Céline Joie; Kristina Deckers; Gerhard Raabe; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2014-06-01       Impact factor: 3.157

7.  Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction.

Authors:  Cheng-Ke Tang; Kai-Xiang Feng; Ai-Bao Xia; Chen Li; Ya-Yun Zheng; Zhen-Yuan Xu; Dan-Qian Xu
Journal:  RSC Adv       Date:  2018-01-17       Impact factor: 3.361

8.  Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines.

Authors:  Chittaranjan Bhanja; Satyaban Jena; Sabita Nayak; Seetaram Mohapatra
Journal:  Beilstein J Org Chem       Date:  2012-10-04       Impact factor: 2.883

9.  A quadruple cascade protocol for the one-pot synthesis of fully-substituted hexahydroisoindolinones from simple substrates.

Authors:  Hong-Bo Zhang; Yong-Chun Luo; Xiu-Qin Hu; Yong-Min Liang; Peng-Fei Xu
Journal:  Beilstein J Org Chem       Date:  2016-02-11       Impact factor: 2.883

Review 10.  Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes.

Authors:  Zhonglei Wang
Journal:  Molecules       Date:  2019-09-19       Impact factor: 4.411

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