Literature DB >> 28349159

Recent applications of the 1,2-carbon atom migration strategy in complex natural product total synthesis.

Xiao-Ming Zhang1, Yong-Qiang Tu, Fu-Min Zhang, Zhi-Hua Chen, Shao-Hua Wang.   

Abstract

1,2-Carbon atom rearrangement has been broadly applied as a guiding strategy in complex molecule assembly. As it entails the carbon-carbon or carbon-heteroatom bond migration between two vicinal atoms, this type of reaction is capable of generating structural complexity through a molecular skeletal reorganization. This review will focus on recent employment of this strategy in the total synthesis of natural products, highlighting the exceptional utility of such synthetic methodologies in the construction of intricate carbocycles, heterocycles or structurally complex motifs from synthetically more accessible precursors.

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Year:  2017        PMID: 28349159     DOI: 10.1039/c6cs00935b

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  12 in total

1.  Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

Authors:  Kevin Hung; Matthew L Condakes; Luiz F T Novaes; Stephen J Harwood; Takahiro Morikawa; Zhi Yang; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-02-11       Impact factor: 15.419

2.  Asymmetric Total Syntheses of Di- and Sesquiterpenoids by Catalytic C-C Activation of Cyclopentanones.

Authors:  Si-Hua Hou; Adriana Y Prichina; Mengxi Zhang; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-12       Impact factor: 15.336

3.  Enantioselective Aryl-Iodide-Catalyzed Wagner-Meerwein Rearrangements.

Authors:  Hayden A Sharma; Katrina M Mennie; Eugene E Kwan; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-09-03       Impact factor: 15.419

Review 4.  Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step.

Authors:  Bastien Delayre; Qian Wang; Jieping Zhu
Journal:  ACS Cent Sci       Date:  2021-04-08       Impact factor: 14.553

5.  Electrophilic Fluorination of Alkenes via Bora-Wagner-Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates.

Authors:  Qiang Wang; Maria Biosca; Fahmi Himo; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-10       Impact factor: 16.823

6.  Reversal of reaction type selectivity by Lewis acid coordination: the ortho photocycloaddition of 1- and 2-naphthaldehyde.

Authors:  Simone Stegbauer; Noah Jeremias; Christian Jandl; Thorsten Bach
Journal:  Chem Sci       Date:  2019-07-29       Impact factor: 9.825

Review 7.  Flow Photochemistry as a Tool in Organic Synthesis.

Authors:  Thomas H Rehm
Journal:  Chemistry       Date:  2020-10-01       Impact factor: 5.236

8.  Identification and Evaluation of Apoptosis-Inducing Activity of Ipomone from Ipomoea nil: A Novel, Unusual Bicyclo-[3.2.1] Octanone Containing Gibberic Acid Diterpenoid.

Authors:  Bharat Goel; Essha Chatterjee; Biswajit Dey; Nancy Tripathi; Nivedita Bhardwaj; Arun Khattri; Santosh Kumar Guru; Shreyans K Jain
Journal:  ACS Omega       Date:  2021-03-15

9.  Catalytic asymmetric synthesis of 3,2'-pyrrolinyl spirooxindoles via conjugate addition/Schmidt-type rearrangement of vinyl azides and (E)-alkenyloxindoles.

Authors:  Ziwei Zhong; Zhijie Xiao; Xiaohua Liu; Weidi Cao; Xiaoming Feng
Journal:  Chem Sci       Date:  2020-09-28       Impact factor: 9.825

Review 10.  Recent development and applications of semipinacol rearrangement reactions.

Authors:  Xiao-Ming Zhang; Bao-Sheng Li; Shao-Hua Wang; Kun Zhang; Fu-Min Zhang; Yong-Qiang Tu
Journal:  Chem Sci       Date:  2021-06-28       Impact factor: 9.825

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