Literature DB >> 30855044

Recent advances in the synthesis of gem-dimethylcyclobutane natural products.

Erin N Hancock1, Johannes M Wiest, M Kevin Brown.   

Abstract

Covering: January 2000 to July 2018 gem-Dimethylcyclobutanes are a common motif found in a multitude of natural products, and thus these structures have captivated synthetic chemists for years. However, until the turn of the century, most synthetic efforts relied upon the use of widely available terpenes, such as pinene or caryophyllene, that already contain the gem-dimethylcyclobutane motif. This approach limits the scope of molecules that can be accessed readily. This review highlights recent syntheses in which the gem-dimethylcyclobutane is assembled via de novo approaches. An outlook on the future of this research area is also provided.

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Year:  2019        PMID: 30855044      PMCID: PMC6739199          DOI: 10.1039/c8np00083b

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  76 in total

1.  Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-11-08       Impact factor: 15.419

2.  Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

Authors:  B V Subba Reddy; Leleti Rajender Reddy; E J Corey
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

3.  Total synthesis of atrochamins F, H, I, and J through cascade reactions.

Authors:  K C Nicolaou; Troy Lister; Ross M Denton; Christine F Gelin
Journal:  Tetrahedron       Date:  2008-05-19       Impact factor: 2.457

4.  Total synthesis of the tetracyclic sesquiterpene (+/-)-punctaporonin C.

Authors:  Martin Fleck; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Samarium(II)-mediated 4-exo-trig cyclization. A stereocontrolled approach to the core of pestalotiopsin A.

Authors:  D Johnston; N Francon; D J Edmonds; D J Procter
Journal:  Org Lett       Date:  2001-06-28       Impact factor: 6.005

6.  Efficient and novel one-pot synthesis of polycycles bearing cyclols by FeCl3-promoted [2 + 2] cycloaddition: application to cannabicyclol, cannabicyclovarin, and ranhuadujuanine A.

Authors:  Xin Li; Yong Rok Lee
Journal:  Org Biomol Chem       Date:  2014-02-28       Impact factor: 3.876

7.  Local anaesthetic activity of beta-caryophyllene.

Authors:  C Ghelardini; N Galeotti; L Di Cesare Mannelli; G Mazzanti; A Bartolini
Journal:  Farmaco       Date:  2001 May-Jul

8.  Total synthesis of punctaporonin C by a regio- and stereoselective [2+2]-photocycloaddition.

Authors:  Martin Fleck; Thorsten Bach
Journal:  Chemistry       Date:  2010-05-25       Impact factor: 5.236

Review 9.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

10.  New isoprenylated flavones, artochamins A--E, and cytotoxic principles from Artocarpus chama.

Authors:  Yong-Hong Wang; Ai-Jun Hou; Lei Chen; Dao-Feng Chen; Han-Dong Sun; Qin-Shi Zhao; Kenneth F Bastow; Yuka Nakanish; Xi-Hong Wang; Kuo-Hsiung Lee
Journal:  J Nat Prod       Date:  2004-05       Impact factor: 4.050

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