Literature DB >> 20095555

Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine.

Nicholas R Perl1, Nathan D Ide, Sudeep Prajapati, Hahdi H Perfect, Sergio G Durón, David Y Gin.   

Abstract

A convergent synthesis of (-)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20095555      PMCID： PMC2839241          DOI： 10.1021/ja910831k

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


  7 in total

1.  The catalytic hydroamination of alkynes.

Authors:  Frauke Pohlki; Sven Doye
Journal:  Chem Soc Rev       Date:  2003-03       Impact factor: 54.564

2.  Isoindoles and dihydroisoquinolines by gold-catalyzed intramolecular hydroamination of alkynes.

Authors:  Daniel Kadzimirsz; Dirk Hildebrandt; Klaus Merz; Gerald Dyker
Journal:  Chem Commun (Camb)       Date:  2006-01-12       Impact factor: 6.222

Review 3.  Hydroamination: direct addition of amines to alkenes and alkynes.

Authors:  Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal:  Chem Rev       Date:  2008-08-26       Impact factor: 60.622

4.  Total synthesis of crambescidin 359.

Authors:  Kazuo Nagasawa; Angelina Georgieva; Hiroyuki Koshino; Tadashi Nakata; Tetsuya Kita; Yuichi Hashimoto
Journal:  Org Lett       Date:  2002-01-24       Impact factor: 6.005

5.  Total synthesis of (-)-crambidine and definition of the relative configuration of its unique tetracyclic guanidinium core.

Authors:  Larry E Overman; Young Ho Rhee
Journal:  J Am Chem Soc       Date:  2005-11-09       Impact factor: 15.419

6.  A synthetic approach to nomofungin/communesin B.

Authors:  Seth L Crawley; Raymond L Funk
Journal:  Org Lett       Date:  2003-09-04       Impact factor: 6.005

7.  Polycyclic guanidine alkaloids from the marine sponge Crambe crambe and Ca++ channel blocker activity of crambescidin 816.

Authors:  R G Berlinck; J C Braekman; D Daloze; I Bruno; R Riccio; S Ferri; S Spampinato; E Speroni
Journal:  J Nat Prod       Date:  1993-07       Impact factor: 4.050
  7 in total
  9 in total

1.  Cationic dirhodium carboxylate-catalyzed synthesis of dihydropyrimidones from propargyl ureas.

Authors:  Miao Yang; Shannon J Odelberg; Zongzhong Tong; Dean Y Li; Ryan E Looper
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

2.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

3.  Regioselective rhodium(II)-catalyzed hydroaminations of propargylguanidines.

Authors:  Morgan J Gainer; Nitasha R Bennett; Yu Takahashi; Ryan E Looper
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-09       Impact factor: 15.336

4.  Synthesis of Cyclic Guanidines via Silver-Catalyzed Intramolecular Alkene Hydroamination Reactions of N-Allylguanidines.

Authors:  Zachary J Garlets; Mattia Silvi; John P Wolfe
Journal:  Org Lett       Date:  2016-05-11       Impact factor: 6.005

5.  The iron-catalyzed construction of 2-aminopyrimidines from alkynenitriles and cyanamides.

Authors:  Timothy K Lane; Minh H Nguyen; Brendan R D'Souza; Nathan A Spahn; Janis Louie
Journal:  Chem Commun (Camb)       Date:  2013-09-11       Impact factor: 6.222

Review 6.  The Oxepane Motif in Marine Drugs.

Authors:  Héctor Barbero; Carlos Díez-Poza; Asunción Barbero
Journal:  Mar Drugs       Date:  2017-11-15       Impact factor: 5.118

7.  ESI-MS Analysis of Thiol-yne Click Reaction in Petroleum Medium.

Authors:  Evgeniya S Degtyareva; Julia V Burykina; Valentine P Ananikov
Journal:  Molecules       Date:  2021-05-13       Impact factor: 4.411

Review 8.  Polycyclic Guanidine Alkaloids from Poecilosclerida Marine Sponges.

Authors:  Estelle Sfecci; Thierry Lacour; Philippe Amade; Mohamed Mehiri
Journal:  Mar Drugs       Date:  2016-04-09       Impact factor: 5.118

9.  Cu-catalyzed asymmetric addition of alcohols to β,γ-alkynyl-α-imino esters for the construction of linear chiral N,O-ketals.

Authors:  Cheng Sheng; Zheng Ling; Yicong Luo; Wanbin Zhang
Journal:  Nat Commun       Date:  2022-01-20       Impact factor: 14.919
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.