Literature DB >> 20481611

Seebach's conjunctive reagent enables double cyclizations.

Brent D Chandler1, Jason T Roland, Yukai Li, Erik J Sorensen.   

Abstract

When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.

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Year:  2010        PMID： 20481611      PMCID： PMC3230265          DOI： 10.1021/ol100845z

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


  9 in total

1.  New anti-HIV derivatives: synthesis and antiviral evaluation.

Authors:  C De Michelis; L Rocheblave; G Priem; J C Chermann; J L Kraus
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2.  New conjunctive reagents as cross-coupling partners en route to retinoid-like polyenes.

Authors:  Bruce H Lipshutz; Giuliano C Clososki; Will Chrisman; David W Chung; David B Ball; Jennifer Howell
Journal:  Org Lett       Date:  2005-10-13       Impact factor: 6.005

3.  Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: total synthesis of (+/-)-clusianone(1).

Authors:  Ji Qi; John A Porco
Journal:  J Am Chem Soc       Date:  2007-09-29       Impact factor: 15.419

4.  One-pot synthesis of adamantane derivatives by domino Michael reactions from ethyl 2,4-dioxocyclohexanecarboxylate.

Authors:  Ryukichi Takagi; Yukiko Miwa; Shuji Matsumura; Katsuo Ohkata
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

5.  Room temperature palladium-catalyzed intramolecular hydroamination of unactivated alkenes.

Authors:  Forrest E Michael; Brian M Cochran
Journal:  J Am Chem Soc       Date:  2006-04-05       Impact factor: 15.419

6.  Absolute stereochemistry of citrinadins a and B from marine-derived fungus.

Authors:  Takao Mugishima; Masashi Tsuda; Yuu Kasai; Haruaki Ishiyama; Eri Fukushi; Jun Kawabata; Masayuki Watanabe; Kenichi Akao; Jun'ichi Kobayashi
Journal:  J Org Chem       Date:  2005-11-11       Impact factor: 4.354

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

Authors:  Martin Pettersson; Daniel Knueppel; Stephen F Martin
Journal:  Org Lett       Date:  2007-10-06       Impact factor: 6.005

Review 8.  Evolution of multi-component anion relay chemistry (ARC): construction of architecturally complex natural and unnatural products.

Authors:  Amos B Smith; William M Wuest
Journal:  Chem Commun (Camb)       Date:  2008-09-30       Impact factor: 6.222

9.  Multicomponent type II anion relay chemistry (ARC): one-pot syntheses of 2,3-disubstituted furans and thiophenes.

Authors:  Nelmi O Devarie-Baez; Won-Suk Kim; Amos B Smith; Ming Xian
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005
  9 in total
  5 in total

1.  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

2.  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

3.  Diastereoselective syntheses of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions.

Authors:  Junjia Liu; Maurice A Marsini; T Aaron Bedell; Paul J Reider; Erik J Sorensen
Journal:  Tetrahedron       Date:  2016-03-15       Impact factor: 2.457

4.  Concise, stereocontrolled synthesis of the citrinadin B core architecture.

Authors:  Carlos A Guerrero; Erik J Sorensen
Journal:  Org Lett       Date:  2011-09-06       Impact factor: 6.005

5.  Enantioselective total syntheses of citrinadins A and B. Stereochemical revision of their assigned structures.

Authors:  Zhiguo Bian; Christopher C Marvin; Martin Pettersson; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2014-09-29       Impact factor: 15.419
  5 in total

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