Literature DB >> 11796044

Total synthesis of crambescidin 359.

Kazuo Nagasawa1, Angelina Georgieva, Hiroyuki Koshino, Tadashi Nakata, Tetsuya Kita, Yuichi Hashimoto.   

Abstract

[structure: see text] Crambescidin 359 (4), which is the "vessel part" of the pentacyclic guanidine alkaloid ptilomycalin A (1), was synthesized for the first time based upon successive 1,3-dipolar cycloaddition reaction. This synthesis established the absolute stereochemistry of 4.

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Year:  2002        PMID: 11796044     DOI: 10.1021/ol0168263

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


  6 in total

Review 1.  Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids.

Authors:  Yunlong Shi; Yasamin Moazami; Joshua G Pierce
Journal:  Bioorg Med Chem       Date:  2017-03-12       Impact factor: 3.641

2.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

3.  A Sequential Cycloaddition Strategy for the Synthesis of Alsmaphorazine B Traces a Path Through a Family of Alstonia Alkaloids.

Authors:  Allen Y Hong; Christopher D Vanderwal
Journal:  Tetrahedron       Date:  2016-11-03       Impact factor: 2.457

4.  Concise synthesis of guanidine-containing heterocycles using the Biginelli reaction.

Authors:  Bradley L Nilsson; Larry E Overman
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

5.  Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine.

Authors:  Nicholas R Perl; Nathan D Ide; Sudeep Prajapati; Hahdi H Perfect; Sergio G Durón; David Y Gin
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

Review 6.  The Oxepane Motif in Marine Drugs.

Authors:  Héctor Barbero; Carlos Díez-Poza; Asunción Barbero
Journal:  Mar Drugs       Date:  2017-11-15       Impact factor: 5.118

  6 in total

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