Literature DB >> 26356301

Total syntheses of natural products containing spirocarbocycles.

Laura K Smith1, Ian R Baxendale.   

Abstract

The structures of natural products from a variety of sources contain spirocycles, two rings that share a common atom. The spiro motif is finding increasing inclusion in drug candidates, and as a structural component in several promising classes of chiral ligands used in asymmetric synthesis. Total syntheses of products containing all-carbon spirocycles feature several common methods of ring closure which we examine in this review.

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Year:  2015        PMID： 26356301     DOI： 10.1039/c5ob01524c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  14 in total

1.  Pd-catalyzed arylation of linear and angular spirodiamine salts under aerobic conditions.

Authors:  Sean W Reilly; Nikaela W Bryan; Robert H Mach
Journal:  Tetrahedron Lett       Date:  2016-12-23       Impact factor: 2.415

2.  Stereodivergent Attached-Ring Synthesis via Non-Covalent Interactions: A Short Formal Synthesis of Merrilactone A.

Authors:  Benjamin J Huffman; Tiffany Chu; Yusuke Hanaki; Jonathan J Wong; Shuming Chen; Kendall N Houk; Ryan A Shenvi
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-09       Impact factor: 15.336

3.  A consecutive synthesis of spiro[cyclopenta[b]pyrrole-5,2'-indene] derivatives via spirocyclization/annulation reactions.

Authors:  Azadeh Parhami; Issa Yavari; Gholam Reza Najafi
Journal:  Mol Divers       Date:  2022-10-12       Impact factor: 3.364

4.  Rh(i)-catalyzed dimerization of ene-vinylidenecyclopropanes for the construction of spiro[4,5]decanes and mechanistic studies.

Authors:  Chao Ning; Kang-Hua Rui; Yin Wei; Min Shi
Journal:  Chem Sci       Date:  2022-06-01       Impact factor: 9.969

5.  Asymmetric Synthesis of All-Carbon Quaternary Spirocycles via a Catalytic Enantioselective Allylic Alkylation Strategy.

Authors:  Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2017-07-05       Impact factor: 2.415

6.  Construction of NH-Unprotected Spiropyrrolidines and Spiroisoindolines by [4+1] Cyclizations of γ-Azidoboronic Acids with Cyclic N-Sulfonylhydrazones.

Authors:  Lucía López; María-Paz Cabal; Carlos Valdés
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-25       Impact factor: 16.823

7.  Catalytic Asymmetric Spirocyclizing Diels-Alder Reactions of Enones: Stereoselective Total and Formal Syntheses of α-Chamigrene, β-Chamigrene, Laurencenone C, Colletoic Acid, and Omphalic Acid.

Authors:  Santanu Ghosh; Johannes Eike Erchinger; Rajat Maji; Benjamin List
Journal:  J Am Chem Soc       Date:  2022-04-07       Impact factor: 16.383

8.  Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy.

Authors:  Luuk Steemers; Martin J Wanner; Martin Lutz; Henk Hiemstra; Jan H van Maarseveen
Journal:  Nat Commun       Date:  2017-05-25       Impact factor: 14.919

9.  Exploring the mechanism of the Pd-catalyzed spirocyclization reaction: a combined DFT and experimental study.

Authors:  Ivan Franzoni; Hyung Yoon; José-Antonio García-López; Amalia Isabel Poblador-Bahamonde; Mark Lautens
Journal:  Chem Sci       Date:  2017-12-08       Impact factor: 9.825

Review 10.  Spirocyclic Motifs in Natural Products.

Authors:  Evgeny Chupakhin; Olga Babich; Alexander Prosekov; Lyudmila Asyakina; Mikhail Krasavin
Journal:  Molecules       Date:  2019-11-17       Impact factor: 4.411
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