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Literature DB >> 19449885

Total synthesis of (-)-agelastatin A: the application of a sequential sigmatropic rearrangement.

Naoto Hama¹, Tomoki Matsuda, Takaaki Sato, Noritaka Chida.

Abstract

An enantioselective total synthesis of (-)-agelastatin A from (-)-2,3-O-isopropylidene-d-threitol is described. The sequential Overman/Mislow-Evans rearrangement of the allylic bistrichloroimidate is the key step, which efficiently installed a diaminohydroxy group.

Entities: Chemical

Year: 2009 PMID： 19449885 DOI： 10.1021/ol900799e

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

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Cited

12 in total

1. Syntheses of Cyclic Guanidine-Containing Natural Products.

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

2. Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction.

Authors: Nels C Gerstner; Jennifer M Schomaker
Journal: J Org Chem Date: 2019-10-16 Impact factor: 4.354

3. Bioinspired total synthesis of agelastatin A.

Authors: Jeremy Chris P Reyes; Daniel Romo
Journal: Angew Chem Int Ed Engl Date: 2012-06-11 Impact factor: 15.336

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

Authors: Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal: Nat Prod Rep Date: 2011-05-09 Impact factor: 13.423

Total synthesis of (-)-agelastatin A: the application of a sequential sigmatropic rearrangement.

1. Syntheses of Cyclic Guanidine-Containing Natural Products.

2. Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction.

3. Bioinspired total synthesis of agelastatin A.

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

Review 5. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

6. Total synthesis of all (-)-Agelastatin alkaloids.

7. Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Review 8. Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

Review 9. A submarine journey: the pyrrole-imidazole alkaloids.

10. Formal synthesis of (-)-agelastatin A: an iron(II)-mediated cyclization strategy.