Literature DB >> 21761893

Directed heterodimerization: stereocontrolled assembly via solvent-caged unsymmetrical diazene fragmentation.

Mohammad Movassaghi1, Omar K Ahmad, Stephen P Lathrop.   

Abstract

A general strategy for the directed and stereocontrolled assembly of carbon-carbon linked heterodimeric hexahydropyrroloindoles is described. The stepwise union of complex amines in the form of mixed diazenes followed by photoexpulsion of dinitrogen in a solvent cage provides completely guided assembly at challenging C(sp(3))-C(sp(3)) and C(sp(3))-C(sp(2)) connections.

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 21761893      PMCID: PMC3157567          DOI: 10.1021/ja2057852

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


  30 in total

1.  Total synthesis of kapakahine E and F.

Authors:  Vinson R Espejo; Jon D Rainier
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

2.  Pyrrolidinoindoline alkaloids from Psychotria oleoides and Psychotria lyciiflora.

Authors:  V Jannic; F Guéritte; O Laprévote; L Serani; M T Martin; T Sévenet; P Potier
Journal:  J Nat Prod       Date:  1999-06       Impact factor: 4.050

3.  Total synthesis of (+)-chaetocin and its analogues: their histone methyltransferase G9a inhibitory activity.

Authors:  Eriko Iwasa; Yoshitaka Hamashima; Shinya Fujishiro; Eisuke Higuchi; Akihiro Ito; Minoru Yoshida; Mikiko Sodeoka
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

4.  Thermolysis of free-radical initiators: tert-butylazocumene and its 1,3- and 1,4-bisazo and 1,3,5-trisazo analogues.

Authors:  P S Engel; L Pan; Y Ying; L B Alemany
Journal:  J Am Chem Soc       Date:  2001-04-25       Impact factor: 15.419

5.  Concise total synthesis and structural revision of (+)-pestalazine B.

Authors:  Carlos Pérez-Balado; Angel R de Lera
Journal:  Org Biomol Chem       Date:  2010-09-17       Impact factor: 3.876

6.  Total synthesis guided structure elucidation of (+)-psychotetramine.

Authors:  Klement Foo; Timothy Newhouse; Ikue Mori; Hiromitsu Takayama; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-17       Impact factor: 15.336

7.  Cyclopropylazetoindolines as precursors to C(3)-quaternary-substituted indolines.

Authors:  Vinson R Espejo; Xi-Bo Li; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

8.  Total synthesis of (+)-11,11'-dideoxyverticillin A.

Authors:  Justin Kim; James A Ashenhurst; Mohammad Movassaghi
Journal:  Science       Date:  2009-04-10       Impact factor: 47.728

9.  Stereocontrolled and versatile total synthesis of bispyrrolidinoindoline diketopiperazine alkaloids: structural revision of the fungal isolate (+)-asperdimin.

Authors:  Carlos Pérez-Balado; Paula Rodríguez-Graña; Angel R de Lera
Journal:  Chemistry       Date:  2009-09-28       Impact factor: 5.236

10.  Total synthesis of (+/-)-psychotrimine.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-07-26       Impact factor: 15.419

View more
  27 in total

1.  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

2.  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

Review 3.  Radical-mediated dimerization and oxidation reactions for the synthesis of complex alkaloids.

Authors:  Stephen P Lathrop; Justin Kim; Mohammad Movassaghi
Journal:  Chimia (Aarau)       Date:  2012       Impact factor: 1.509

4.  Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.

Authors:  Stephen P Lathrop; Matthew Pompeo; Wen-Tau T Chang; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-06-14       Impact factor: 15.419

5.  Studies towards the total synthesis of drimentine C. Preparation of the AB and CDEF ring fragments.

Authors:  Sarah M Pound; Steven J Underwood; Christopher J Douglas
Journal:  European J Org Chem       Date:  2020-03-19

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.  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

8.  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

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.  Additive- and Metal-Free, Predictably 1,2- and 1,3-Regioselective, Photoinduced Dual C-H/C-X Borylation of Haloarenes.

Authors:  Adelphe M Mfuh; Vu T Nguyen; Bhuwan Chhetri; Jessica E Burch; John D Doyle; Vladimir N Nesterov; Hadi D Arman; Oleg V Larionov
Journal:  J Am Chem Soc       Date:  2016-07-01       Impact factor: 15.419

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.