Literature DB >> 26334685

Direct construction of vicinal all-carbon quaternary stereocenters in natural product synthesis.

Rong Long1, Jun Huang, Jianxian Gong, Zhen Yang.   

Abstract

Molecules containing vicinal all-carbon quaternary stereocenters are found in many secondary metabolites, and they exhibit a variety of biological and pharmacological activities. However, the construction of such a structural motif remains a significant challenge in natural product synthesis. Only in recent years have considerable efforts been made to construct vicinal quaternary stereocenters in a single-step operation. In this review, we focus on the different types of methods that have been successfully used in the total synthesis of natural products. Based on the classified reactions for the simultaneous generation of vicinal all-carbon quaternary stereocenters, the total syntheses of the natural products are discussed, placing emphasis on the diastereoselective preparation of vicinal quaternary carbon centers and the subsequent total syntheses.

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Year:  2015        PMID: 26334685     DOI: 10.1039/c5np00046g

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  19 in total

1.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

2.  Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.

Authors:  Joseph M Zanghi; Shuang Liu; Simon J Meek
Journal:  Org Lett       Date:  2019-06-14       Impact factor: 6.005

3.  Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers.

Authors:  Jose M Medina; Jesus Moreno; Sophie Racine; Shuaijing Du; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-03       Impact factor: 15.336

4.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

5.  Stereoselective α-Tertiary Alkylation of N-(Arylacetyl)oxazolidinones.

Authors:  Eunjae Shim; Armen Zakarian
Journal:  Synlett       Date:  2020-04       Impact factor: 2.454

6.  Taming Radical Pairs in the Crystalline Solid State: Discovery and Total Synthesis of Psychotriadine.

Authors:  Jordan J Dotson; Ieva Liepuoniute; J Logan Bachman; Vince M Hipwell; Saeed I Khan; K N Houk; Neil K Garg; Miguel A Garcia-Garibay
Journal:  J Am Chem Soc       Date:  2021-03-08       Impact factor: 15.419

7.  Enantio- and diastereoselective diarylmethylation of 1,3-dicarbonyl compounds.

Authors:  Xin Li; Songtao He; Qiuling Song
Journal:  Chem Sci       Date:  2020-05-25       Impact factor: 9.825

Review 8.  Catalytic enantioselective construction of vicinal quaternary carbon stereocenters.

Authors:  Feng Zhou; Lei Zhu; Bo-Wen Pan; Yang Shi; Yun-Lin Liu; Jian Zhou
Journal:  Chem Sci       Date:  2020-07-28       Impact factor: 9.825

9.  Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols.

Authors:  Shengtong Niu; Hao Zhang; Weici Xu; Prasanta Ray Bagdi; Guoxiang Zhang; Jinggong Liu; Shuang Yang; Xinqiang Fang
Journal:  Nat Commun       Date:  2021-06-18       Impact factor: 14.919

Review 10.  Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances.

Authors:  Thiago S Silva; Fernando Coelho
Journal:  Beilstein J Org Chem       Date:  2021-07-07       Impact factor: 2.883

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