Literature DB >> 20161427

Enantioselective synthesis of Bakuchiol using diazosulfonate C-H insertion to install the quaternary center.

Joseph P Bequette1, Christian S Jungong, Alexei V Novikov.   

Abstract

Bakuchiol was prepared from commercial (-)-citronellol using the diazosulfonate C-H insertion to control the regioselectivity and install the quaternary center.

Entities:  

Year:  2009        PMID： 20161427      PMCID： PMC2786188          DOI： 10.1016/j.tetlet.2009.09.147

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  4 in total

1.  Synthesis and structure-immunosuppressive activity relationships of bakuchiol and its derivatives.

Authors:  Hongli Chen; Xiaolong Du; Wei Tang; Yu Zhou; Jianping Zuo; Huijin Feng; Yuanchao Li
Journal:  Bioorg Med Chem       Date:  2007-11-28       Impact factor: 3.641

2.  Synthesis of (+)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]oct-3-ene, an optically active form of the house mouse pheromone.

Authors:  Y Masaki; I Iwata; T Imaeda; H Oda; H Nagashima
Journal:  Chem Pharm Bull (Tokyo)       Date:  1988-03       Impact factor: 1.645

3.  Selective formation of six-membered cyclic sulfones and sulfonates by C-H insertion.

Authors:  Jinu P John; Alexei V Novikov
Journal:  Org Lett       Date:  2007-01-04       Impact factor: 6.005

4.  Delta-sultone formation through Rh-catalyzed C-H insertion.

Authors:  Scott A Wolckenhauer; A Sloan Devlin; J Du Bois
Journal:  Org Lett       Date:  2007-09-21       Impact factor: 6.005
  4 in total
  6 in total

1.  Aliphatic C-H to C-C conversion: synthesis of (-)-cameroonan-7α-ol.

Authors:  Douglass F Taber; Christopher G Nelson
Journal:  J Org Chem       Date:  2011-02-23       Impact factor: 4.354

2.  Synthesis of quaternary carbon stereogenic centers through enantioselective Cu-catalyzed allylic substitutions with vinylaluminum reagents.

Authors:  Fang Gao; Kevin P McGrath; Yunmi Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

3.  SYNTHETICALLY USEFUL INTERMEDIATES BY DIAZOSULFONE AND SULFONATE C-H INSERTION.

Authors:  Duminda S Liyanage; Christian S Jungong; Alexei V Novikov
Journal:  Synth Commun       Date:  2015-01-17       Impact factor: 2.007

Review 4.  Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades.

Authors:  Cheng-Shi Jiang; Lin-fu Liang; Yue-wei Guo
Journal:  Acta Pharmacol Sin       Date:  2012-09-03       Impact factor: 6.150

Review 5.  Bakuchiol - a natural meroterpenoid: structure, isolation, synthesis and functionalization approaches.

Authors:  T P Adarsh Krishna; Baldev Edachery; Sunil Athalathil
Journal:  RSC Adv       Date:  2022-03-21       Impact factor: 3.361

6.  Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated Claisen rearrangement and total synthesis of (+)-bakuchiol.

Authors:  Ken-ichi Takao; Shu Sakamoto; Marianne Ayaka Touati; Yusuke Kusakawa; Kin-ichi Tadano
Journal:  Molecules       Date:  2012-11-08       Impact factor: 4.411
  6 in total

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