Literature DB >> 17918954

Concise, stereoselective approach to the spirooxindole ring system of citrinadin A.

Martin Pettersson1, Daniel Knueppel, Stephen F Martin.   

Abstract

The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter. The key step involves a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17918954     DOI： 10.1021/ol702132v

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


  14 in total

1.  Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.

Authors:  Sunkyu Han; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-10-31       Impact factor: 4.354

2.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors:  Stephen F Martin
Journal:  J Org Chem       Date:  2017-09-15       Impact factor: 4.354

3.  Seebach's conjunctive reagent enables double cyclizations.

Authors:  Brent D Chandler; Jason T Roland; Yukai Li; Erik J Sorensen
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

4.  Synthetic studies toward the citrinadin A and B core architecture.

Authors:  Devon A Mundal; Richmond Sarpong
Journal:  Org Lett       Date:  2013-09-19       Impact factor: 6.005

5.  Concise total synthesis and stereochemical revision of all (-)-trigonoliimines.

Authors:  Sunkyu Han; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2011-06-20       Impact factor: 15.419

6.  Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

Authors:  Zhiguo Bian; Christopher C Marvin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

7.  An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B.

Authors:  Ke Kong; John A Enquist; Monica E McCallum; Genessa M Smith; Takanori Matsumaru; Elnaz Menhaji-Klotz; John L Wood
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

8.  Chemoselective and enantioselective oxidation of indoles employing aspartyl peptide catalysts.

Authors:  Filip Kolundzic; Mohammad N Noshi; Meiliana Tjandra; Mohammad Movassaghi; Scott J Miller
Journal:  J Am Chem Soc       Date:  2011-05-23       Impact factor: 15.419

9.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

Review 10.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.