Literature DB >> 19317498

Concise enantioselective synthesis of ent-malbrancheamide B.

Frederic Frebault1, Nigel S Simpkins, Ashley Fenwick.   

Abstract

A concise enantioselective synthesis of the fungal metabolite ent-malbrancheamide B was accomplished through the union of a C-prenylated proline derivative and a substituted indole pyruvic acid SEM enol ether, followed by a cationic double cyclization as the key step.

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Year:  2009        PMID: 19317498     DOI: 10.1021/ja900688y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  8 in total

Review 1.  Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Authors:  Kenneth A Miller; Robert M Williams
Journal:  Chem Soc Rev       Date:  2009-09-16       Impact factor: 54.564

2.  Synthesis of (+/-)-eusynstyelamide A.

Authors:  Olga V Barykina; Barry B Snider
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

3.  An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides.

Authors:  Brian J Knight; Erin E Stache; Eric M Ferreira
Journal:  Tetrahedron       Date:  2015-05-09       Impact factor: 2.457

4.  Utilizing DART mass spectrometry to pinpoint halogenated metabolites from a marine invertebrate-derived fungus.

Authors:  Katharine R Watts; Steven T Loveridge; Karen Tenney; Joseph Media; Frederick A Valeriote; Phillip Crews
Journal:  J Org Chem       Date:  2011-06-29       Impact factor: 4.354

Review 5.  Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi.

Authors:  Kimberly R Klas; Hikaru Kato; Jens C Frisvad; Fengan Yu; Sean A Newmister; Amy E Fraley; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

6.  Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions.

Authors:  Alejandro Cabanillas; Christopher D Davies; Louise Male; Nigel S Simpkins
Journal:  Chem Sci       Date:  2014-11-28       Impact factor: 9.825

7.  Unified total synthesis of the brevianamide alkaloids enabled by chemical investigations into their biosynthesis.

Authors:  Robert C Godfrey; Helen E Jones; Nicholas J Green; Andrew L Lawrence
Journal:  Chem Sci       Date:  2021-12-29       Impact factor: 9.825

8.  Unified Approach to Prenylated Indole Alkaloids: Total Syntheses of (-)-17-Hydroxy-Citrinalin B, (+)-Stephacidin A, and (+)-Notoamide I.

Authors:  Eduardo V Mercado-Marin; Richmond Sarpong
Journal:  Chem Sci       Date:  2015-06-18       Impact factor: 9.825

  8 in total

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