Literature DB >> 16836414

A formal total synthesis of the marine diterpenoid diisocyanoadociane.

Kelly A Fairweather1, Lewis N Mander.   

Abstract

[Structure: see text] A formal total synthesis of diisocyanoadociane, a marine diterpenoid with potent antimalarial properties, has been completed. The synthesis begins with a phenanthrenoid precursor that is transformed into a pyrene-derived intermediate by means of an intramolecular Michael reaction. Nitrogen functionality is introduced via a double Curtius reaction.

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Year:  2006        PMID： 16836414     DOI： 10.1021/ol061228f

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class.

Authors:  Hai-Hua Lu; Sergey V Pronin; Yevgeniya Antonova-Koch; Stephan Meister; Elizabeth A Winzeler; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2016-05-31       Impact factor: 15.419

2.  Concise Synthesis of the Antiplasmodial Isocyanoterpene 7,20-Diisocyanoadociane.

Authors:  Alexander S Karns; Bryan D Ellis; Philipp C Roosen; Zeinab Chahine; Karine G Le Roch; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-27       Impact factor: 15.336

Review 3.  Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.

Authors:  Martin J Schnermann; Ryan A Shenvi
Journal:  Nat Prod Rep       Date:  2015-04       Impact factor: 13.423

4.  Evolution of a Short and Stereocontrolled Synthesis of (+)-7,20-Diisocyanoadociane.

Authors:  Philipp C Roosen; Alexander S Karns; Bryan D Ellis; Christopher D Vanderwal
Journal:  J Org Chem       Date:  2022-01-06       Impact factor: 4.198

5.  Total synthesis of (±)-maoecrystal V.

Authors:  Feng Peng; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-11-05       Impact factor: 15.419

6.  Toosendanin: synthesis of the AB-ring and investigations of its anti-botulinum properties (Part II).

Authors:  Yuya Nakai; Sabine Pellett; William H Tepp; Eric A Johnson; Kim D Janda
Journal:  Bioorg Med Chem       Date:  2009-12-22       Impact factor: 3.641

Review 7.  The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses.

Authors:  Arun K Ghosh; Anindya Sarkar; Margherita Brindisi
Journal:  Org Biomol Chem       Date:  2018-02-26       Impact factor: 3.876
  7 in total

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