Literature DB >> 26836448

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.

Martin Büschleb1, Stéphane Dorich1, Stephen Hanessian2, Daniel Tao3, Kyle B Schenthal3, Larry E Overman3.   

Abstract

Strategies for the total synthesis of complex natural products that contain two or more contiguous stereogenic quaternary carbon atoms in their intricate structures are reviewed with 12 representative examples. Emphasis has been put on methods to create quaternary carbon stereocenters, including syntheses of the same natural product by different groups, thereby showcasing the diversity of thought and individual creativity. A compendium of selected natural products containing two or more contiguous stereogenic quaternary carbon atoms and key reactions in their total or partial syntheses is provided in the Supporting Information.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  biomimetic synthesis; natural products; quaternary carbon atoms; synthetic methods

Mesh：

Substances：

Year:  2016        PMID： 26836448      PMCID： PMC4865016          DOI： 10.1002/anie.201507549

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  96 in total

1.  Manganese(III)-Based Oxidative Free-Radical Cyclizations.

Authors:  Barry B. Snider
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

Review 2.  Chemistry and biology of biosynthetic Diels-Alder reactions.

Authors:  Emily M Stocking; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-14       Impact factor: 15.336

3.  Total synthesis of (±) maoecrystal V.

Authors:  Jianxian Gong; Guang Lin; Wenbo Sun; Chuang-Chuang Li; Zhen Yang
Journal:  J Am Chem Soc       Date:  2010-11-04       Impact factor: 15.419

4.  Efficient entry to the hasubanan alkaloids: first enantioselective total syntheses of (-)-hasubanonine, (-)-runanine, (-)-delavayine, and (+)-periglaucine B.

Authors:  Seth B Herzon; Nicholas A Calandra; Sandra M King
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-03       Impact factor: 15.336

5.  Chemoenzymatic synthesis and application of bicyclo[2.2.2]octadiene ligands: increased efficiency in rhodium-catalyzed asymmetric conjugate additions by electronic tuning.

Authors:  Yunfei Luo; Andrew J Carnell
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-01       Impact factor: 15.336

6.  Enantioselective total synthesis of (-)-maoecrystal V.

Authors:  Changwu Zheng; Igor Dubovyk; Kiel E Lazarski; Regan J Thomson
Journal:  J Am Chem Soc       Date:  2014-12-11       Impact factor: 15.419

7.  [Antibiotic hyperforin from Hypericum perforatum L].

Authors:  A I Gurevich; V N Dobrynin; M N Kolosov; S A Popravko; I D Riabova
Journal:  Antibiotiki       Date:  1971-06

8.  Tandem cycloaddition reactions of allenyl diazo compounds forming triquinanes via trimethylenemethane diyls.

Authors:  Taek Kang; Won-Yeob Kim; Yeokwon Yoon; Byung Gyu Kim; Hee-Yoon Lee
Journal:  J Am Chem Soc       Date:  2011-10-20       Impact factor: 15.419

9.  Role of glycine receptors and glycine release for the neuroprotective activity of bilobalide.

Authors:  Cornelia Kiewert; Vikas Kumar; Oksana Hildmann; Joachim Hartmann; Markus Hillert; Jochen Klein
Journal:  Brain Res       Date:  2008-01-31       Impact factor: 3.252

10.  Total syntheses of hyperforin and papuaforins A-C, and formal synthesis of nemorosone through a gold(I)-catalyzed carbocyclization.

Authors:  Gabriel Bellavance; Louis Barriault
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-18       Impact factor: 15.336
View more
  37 in total

1.  Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors:  Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal:  European J Org Chem       Date:  2020-01-01

2.  Forging C(sp3)-C(sp3) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

Authors:  Spencer P Pitre; Nicholas A Weires; Larry E Overman
Journal:  J Am Chem Soc       Date:  2019-01-04       Impact factor: 15.419

3.  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

4.  Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines.

Authors:  Petra Lindovska; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2017-11-20       Impact factor: 15.419

5.  Photoinduced Carboborative Ring Contraction Enables Regio- and Stereoselective Synthesis of Multiply Substituted Five-Membered Carbocycles and Heterocycles.

Authors:  Shengfei Jin; Vu T Nguyen; Hang T Dang; Dat P Nguyen; Hadi D Arman; Oleg V Larionov
Journal:  J Am Chem Soc       Date:  2017-08-09       Impact factor: 15.419

6.  Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.

Authors:  Kelvin Pak Shing Cheung; Daria Kurandina; Tetsuji Yata; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

7.  P450-Mediated Coupling of Indole Fragments To Forge Communesin and Unnatural Isomers.

Authors:  Hsiao-Ching Lin; Travis C McMahon; Ashay Patel; Michael Corsello; Adam Simon; Wei Xu; Muxun Zhao; K N Houk; Neil K Garg; Yi Tang
Journal:  J Am Chem Soc       Date:  2016-03-18       Impact factor: 15.419

8.  Lithium Enolates in the Enantioselective Construction of Tetrasubstituted Carbon Centers with Chiral Lithium Amides as Noncovalent Stereodirecting Auxiliaries.

Authors:  Kai Yu; Ping Lu; Jeffrey J Jackson; Thuy-Ai D Nguyen; Joseph Alvarado; Craig E Stivala; Yun Ma; Kyle A Mack; Trevor W Hayton; David B Collum; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2016-12-20       Impact factor: 15.419

9.  Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

Authors:  Robert B Susick; Lucas A Morrill; Elias Picazo; Neil K Garg
Journal:  Synlett       Date:  2017       Impact factor: 2.454

10.  Enantioselective Coupling of Dienes and Phosphine Oxides.

Authors:  Shao-Zhen Nie; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-11-19       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.