Literature DB >> 16402402

The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings.

Merle A Battiste1, Phillip M Pelphrey, Dennis L Wright.   

Abstract

Highly substituted carbocyclic seven-membered rings are frequently found in natural products and their synthesis represents a significant challenge to the synthetic chemist. Direct intramolecular cyclization of these systems often proves difficult and this fact has catalyzed the development of a variety of strategies based on a convergent intermolecular cycloaddition strategy. This concept article discusses the major cycloaddition approaches utilized to access these types of structures and primarily focuses on examples employed in the synthesis of natural products.

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Year:  2006        PMID: 16402402     DOI: 10.1002/chem.200501083

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  35 in total

1.  Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

Authors:  Hongmiao Wu; Weiwei Zi; Guigen Li; Hongjian Lu; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

2.  Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors:  Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal:  J Am Chem Soc       Date:  2012-03-12       Impact factor: 15.419

3.  Intramolecular oxyallyl-carbonyl (3 + 2) cycloadditions.

Authors:  Elizabeth H Krenske; Shuzhong He; Jian Huang; Yunfei Du; K N Houk; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2013-04-01       Impact factor: 15.419

4.  Catalytic Enantioselective Intermolecular [5 + 2] Dipolar Cycloadditions of a 3-Hydroxy-4-pyrone-Derived Oxidopyrylium Ylide.

Authors:  Katherine N Fuhr; Danielle R Hirsch; Ryan P Murelli; Stacey E Brenner-Moyer
Journal:  Org Lett       Date:  2017-11-17       Impact factor: 6.005

5.  Developing a diastereoselective intramolecular [4+3] cycloaddition of nitrogen-stabilized oxyallyl cations derived from N-sulfonyl-substituted allenamides.

Authors:  Andrew G Lohse; Richard P Hsung; Mitchell D Leider; Sunil K Ghosh
Journal:  J Org Chem       Date:  2011-04-08       Impact factor: 4.354

6.  Synthesis of Naturally Occurring Tropones and Tropolones.

Authors:  Na Liu; Wangze Song; Casi M Schienebeck; Min Zhang; Weiping Tang
Journal:  Tetrahedron       Date:  2014-12-09       Impact factor: 2.457

7.  Mechanistic Perspectives in the Regioselective Indole Addition to Unsymmetrical Silyloxyallyl Cations.

Authors:  Caitlin G Bresnahan; Kiara A Taylor-Edinbyrd; Alexander H Cleveland; Joshua A Malone; Nitin S Dange; Anne Milet; Revati Kumar; Rendy Kartika
Journal:  J Org Chem       Date:  2019-05-16       Impact factor: 4.354

8.  Control of regioselectivity and stereoselectivity in (4 + 3) cycloadditions of chiral oxyallyls with unsymmetrically disubstituted furans.

Authors:  Yunfei Du; Elizabeth H Krenske; Jennifer E Antoline; Andrew G Lohse; K N Houk; Richard P Hsung
Journal:  J Org Chem       Date:  2012-07-31       Impact factor: 4.354

9.  Asymmetric synthesis of seven-membered carbocyclic rings via a sequential oxyanionic 5-exo-dig cyclization/claisen rearrangement process. Total synthesis of (-)-frondosin B.

Authors:  Timo V Ovaska; Jonathan A Sullivan; Sami I Ovaska; Jacob B Winegrad; Justin D Fair
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

10.  Conditions for a Rh(I)-catalyzed [2 + 2 + 1] cycloaddition reaction with methyl substituted allenes and alkynes.

Authors:  Sarah M Wells; Kay M Brummond
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

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