Literature DB >> 17602639

Synthesis of (-)-agelastatin A by [3.3] sigmatropic rearrangement of allyl cyanate.

Yoshiyasu Ichikawa1, Tomonori Yamaoka, Keiji Nakano, Hiyoshizo Kotsuki.   

Abstract

Total synthesis of (-)-agelastatin A has been achieved starting from l-arabitol. The highlights in our synthesis include the preparation of vicinal diamine moiety by [3.3] sigmatropic rearrangement of allyl cyanate and construction of central ring-C with ring-closing metathesis.

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Year:  2007        PMID: 17602639     DOI: 10.1021/ol0709735

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


  18 in total

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2.  A chiral Lewis acid strategy for enantioselective allylic C-H oxidation.

Authors:  Dustin J Covell; M Christina White
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Review 3.  Chemistry of polyvalent iodine.

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4.  Syntheses of Cyclic Guanidine-Containing Natural Products.

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5.  Bioinspired total synthesis of agelastatin A.

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Journal:  Angew Chem Int Ed Engl       Date:  2012-06-11       Impact factor: 15.336

6.  Synthesis and anticancer activity of all known (-)-agelastatin alkaloids.

Authors:  Sunkyu Han; Dustin S Siegel; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

Review 7.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

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8.  A stereodivergent strategy to both product enantiomers from the same enantiomer of a stereoinducing catalyst: agelastatin A.

Authors:  Barry M Trost; Guangbin Dong
Journal:  Chemistry       Date:  2009-07-13       Impact factor: 5.236

9.  Total synthesis of (+/-)-agelastatin A, a potent inhibitor of osteopontin-mediated neoplastic transformations.

Authors:  David P Dickson; Duncan J Wardrop
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

Review 10.  A submarine journey: the pyrrole-imidazole alkaloids.

Authors:  Barbara Forte; Beatrice Malgesini; Claudia Piutti; Francesca Quartieri; Alessandra Scolaro; Gianluca Papeo
Journal:  Mar Drugs       Date:  2009-11-27       Impact factor: 5.118

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