Literature DB >> 19374357

Enantiospecific total syntheses of kapakahines B and F.

Timothy Newhouse1, Chad A Lewis, Phil S Baran.   

Abstract

Gram-scale, enantiospecific total syntheses of the anti-leukemia marine natural products kapakahines B and F have been completed. Two powerfully simplifying transformations have enabled the gram-scale synthesis of this natural product family: (1) an oxidative N-C bond-forming reaction that sets a key quaternary center with complete stereocontrol and (2) a unique strategy for the construction of twisted macrocycles via dynamic equilibration of complex late-stage intermediates.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19374357     DOI： 10.1021/ja901573x

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


  21 in total

1.  Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

2.  Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors:  Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

3.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

4.  Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

Authors:  Stephen P Lathrop; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2014-01-01       Impact factor: 9.825

5.  Why do some Fischer indolizations fail?

Authors:  Nihan Çelebi-Ölçüm; Ben W Boal; Alexander D Huters; Neil K Garg; K N Houk
Journal:  J Am Chem Soc       Date:  2011-03-28       Impact factor: 15.419

6.  Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  European J Org Chem       Date:  2014-06-01

7.  Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products.

Authors:  Emily C Gentry; Lydia J Rono; Martina E Hale; Rei Matsuura; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2018-02-21       Impact factor: 15.419

8.  Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Authors:  Ian B Seiple; Shun Su; Ian S Young; Akifumi Nakamura; Junichiro Yamaguchi; Lars Jørgensen; Rodrigo A Rodriguez; Daniel P O'Malley; Tanja Gaich; Matthias Köck; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-08-23       Impact factor: 15.419

9.  Concise Total Synthesis of (+)-Gliocladins B and C.

Authors:  Nicolas Boyer; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2012-03-30       Impact factor: 9.825

10.  Concise Total Synthesis of (+)-Luteoalbusins A and B.

Authors:  Timothy C Adams; Joshua N Payette; Jaime H Cheah; Mohammad Movassaghi
Journal:  Org Lett       Date:  2015-08-25       Impact factor: 6.005
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.