Literature DB >> 19317433

Asymmetric total synthesis of the iridoid beta-glucoside (+)-geniposide via phosphine organocatalysis.

Regan A Jones1, Michael J Krische.   

Abstract

Phosphine-catalyzed [3 + 2] cycloaddition of ethyl-2,3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the cis-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19317433      PMCID： PMC2863135          DOI： 10.1021/ol900360h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  36 in total

1.  Intramolecular organocatalytic [3+2] dipolar cycloaddition: stereospecific cycloaddition and the total synthesis of (+/-)-hirsutene.

Authors:  Jian-Cheng Wang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2003       Impact factor: 15.336

2.  Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model.

Authors:  Barry M Trost; Michelle R Machacek; Aaron Aponick
Journal:  Acc Chem Res       Date:  2006-10       Impact factor: 22.384

3.  Phosphine-catalyzed allylic substitution of Morita-Baylis-Hillman acetates: synthesis of N-protected beta-aminophosphonic acid esters.

Authors:  HaeIl Park; Chang-Woo Cho; Michael J Krische
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

4.  Regio- and stereoselective construction of gamma-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates: an organocatalytic allylic alkylation.

Authors:  Chang-Woo Cho; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-10       Impact factor: 15.336

Review 5.  Naturally occurring iridoids. A review, part 1.

Authors:  Biswanath Dinda; Sudhan Debnath; Yoshihiro Harigaya
Journal:  Chem Pharm Bull (Tokyo)       Date:  2007-02       Impact factor: 1.645

6.  Organocatalytic Michael cycloisomerization of bis(enones): the intramolecular Rauhut-Currier reaction.

Authors:  Long-Cheng Wang; Ana Liza Luis; Kyriacos Agapiou; Hye-Young Jang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

7.  Catalytic crossed Michael cycloisomerization of thioenoates: total synthesis of (+/-)-ricciocarpin A.

Authors:  Kyriacos Agapiou; Michael J Krische
Journal:  Org Lett       Date:  2003-05-15       Impact factor: 6.005

8.  Concise stereocontrolled formal synthesis of (+/-)-quinine and total synthesis of (+/-)-7- hydroxyquinine via merged Morita-Baylis-Hillman-Tsuji-Trost cyclization.

Authors:  Peter Webber; Michael J Krische
Journal:  J Org Chem       Date:  2008-12-05       Impact factor: 4.354

9.  A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides.

Authors:  Ravula Satheesh Babu; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

10.  Catalytic diastereoselective synthesis of diquinanes from acyclic precursors.

Authors:  Jian-Cheng Wang; Sze-Sze Ng; Michael J Krische
Journal:  J Am Chem Soc       Date:  2003-04-02       Impact factor: 15.419
View more
  9 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.

Authors:  Yumei Xiao; Hongchao Guo; Ohyun Kwon
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

3.  Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates.

Authors:  Chengfeng Jing; Risong Na; Bo Wang; Honglei Liu; Lei Zhang; Jun Liu; Min Wang; Jiangchun Zhong; Ohyun Kwon; Hongchao Guo
Journal:  Adv Synth Catal       Date:  2012-04-26       Impact factor: 5.837

Review 4.  Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.

Authors:  Joost N H Reek; Bas de Bruin; Sonja Pullen; Tiddo J Mooibroek; Alexander M Kluwer; Xavier Caumes
Journal:  Chem Rev       Date:  2022-05-20       Impact factor: 72.087

Review 5.  Updated Pharmacological Effects, Molecular Mechanisms, and Therapeutic Potential of Natural Product Geniposide.

Authors:  Liping Liu; Qin Wu; Yuping Chen; Guoxiang Gu; Runan Gao; Bo Peng; Yue Wang; Anbang Li; Jipeng Guo; Xinru Xu; Xiaochen Shao; Lingxing Li; Ya Shen; Jihu Sun
Journal:  Molecules       Date:  2022-05-21       Impact factor: 4.927

6.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2013-12-25       Impact factor: 6.222

Review 7.  Phosphine catalysis of allenes with electrophiles.

Authors:  Zhiming Wang; Xingzhu Xu; Ohyun Kwon
Journal:  Chem Soc Rev       Date:  2014-03-24       Impact factor: 54.564

8.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036

9.  Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine.

Authors:  Huanzhen Ni; Weijun Yao; Yixin Lu
Journal:  Beilstein J Org Chem       Date:  2016-02-24       Impact factor: 2.883
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.