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Literature DB >> 25125710

Enantioselective synthesis of decalin structures with all-carbon quaternary centers via one-pot sequential Cope/Rauhut-Currier reaction.

Tina Morgan Ross¹, Sarah Burke¹, Wlliam P Malachowski¹.

Abstract

The first example of one-pot sequential Cope/Rauhut-Currier reactions are reported and used to make functionalized decalin structures with all-carbon quaternary stereocenters. The substrates for the new sequential reaction are generated through a six-step sequence including an enantioselective Birch reduction-allylation reaction which makes the overall process asymmetric.

Entities: Chemical Disease

Keywords: Cope; Rauhut-Currier; enantioselective; sequential

Year: 2014 PMID： 25125710 PMCID： PMC4127640 DOI： 10.1016/j.tetlet.2014.06.085

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

32 in total

1. Exploration of the enantioselective Birch-Cope sequence for the synthesis of carbocyclic quaternary stereocenters.

Authors: Tapas Paul; William P Malachowski; Jisun Lee
Journal: J Org Chem Date: 2007-02-02 Impact factor: 4.354

2. The enantioselective Birch-Cope sequence for the synthesis of carbocyclic quaternary stereocenters. Application to the synthesis of (+)-mesembrine.

Authors: Tapas Paul; William P Malachowski; Jisun Lee
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

3. Total synthesis of (+)-asperolide C by iridium-catalyzed enantioselective polyene cyclization.

Authors: Oliver F Jeker; Alberto G Kravina; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2013-09-24 Impact factor: 15.336

4. Enantioselective total synthesis of the diterpenes kempene-2, kempene-1, and 3-epi-kempene-1 from the defense secretion of higher termites.

Authors: Melanie Schubert; Peter Metz
Journal: Angew Chem Int Ed Engl Date: 2011-02-25 Impact factor: 15.336

1. The enantioselective construction of tetracyclic diterpene skeletons with Friedel-Crafts alkylation and palladium-catalyzed cycloalkenylation reactions.

Authors: Sarah J Burke; William P Malachowski; Sharan K Mehta; Roselyn Appenteng
Journal: Org Biomol Chem Date: 2015-03-07 Impact factor: 3.876

1 in total

Enantioselective synthesis of decalin structures with all-carbon quaternary centers via one-pot sequential Cope/Rauhut-Currier reaction.

1. Exploration of the enantioselective Birch-Cope sequence for the synthesis of carbocyclic quaternary stereocenters.

2. The enantioselective Birch-Cope sequence for the synthesis of carbocyclic quaternary stereocenters. Application to the synthesis of (+)-mesembrine.

3. Total synthesis of (+)-asperolide C by iridium-catalyzed enantioselective polyene cyclization.

4. Enantioselective total synthesis of the diterpenes kempene-2, kempene-1, and 3-epi-kempene-1 from the defense secretion of higher termites.

Review 5. Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

6. Total synthesis and antibacterial activity of dysidavarone A.

7. Diterpenoids from Croton laui and their cytotoxic and antimicrobial activities.

8. Total synthesis of (+)-crotogoudin.

9. The combined C-H functionalization/Cope rearrangement: discovery and applications in organic synthesis.

10. Concise enantiospecific total synthesis of tubingensin A.

1. The enantioselective construction of tetracyclic diterpene skeletons with Friedel-Crafts alkylation and palladium-catalyzed cycloalkenylation reactions.