Literature DB >> 12841747

Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans.

Conor St J Barry1, Stuart R Crosby, John R Harding, Rachael A Hughes, Clare D King, Gregory D Parker, Christine L Willis.   

Abstract

[reaction: see text] Reaction of homoallylic alcohols with aldehydes in the presence of TFA gives, after hydrolysis of the ester, 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans with the creation of three new stereocenters in a single-pot process. By varying the aldehyde component, a variety of functionalized side chains are installed at C-2. The utility of this approach is extended to the enantioselective synthesis of tetrahydropyrans with >99% ee.

Entities:  

Year:  2003        PMID： 12841747     DOI： 10.1021/ol0346180

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


  9 in total

1.  Racemization in Prins cyclization reactions.

Authors:  Ramesh Jasti; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

2.  Solvolysis of a tetrahydropyranyl mesylate: mechanistic implications for the Prins cyclization, 2-oxonia-cope rearrangement, and Grob fragmentation.

Authors:  Ramesh Jasti; Scott D Rychnovsky
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

3.  A Novel Trisubstituted Tetrahydropyran as a Possible Pheromone Component for the South American Cerambycid Beetle Macropophora accentifer.

Authors:  Weliton D Silva; Yunfan Zou; Lawrence M Hanks; José Maurício S Bento; Jocelyn G Millar
Journal:  J Chem Ecol       Date:  2022-04-30       Impact factor: 2.793

4.  Rhenium(VII) catalysis of Prins cyclization reactions.

Authors:  Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

5.  Symmetric macrocycles by a Prins dimerization and macrocyclization strategy.

Authors:  Michael R Gesinski; Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

6.  FeCl3-Catalyzed Tandem Prins and Friedel-Crafts Cyclization: A Highly Diastereoselective Route to Polycyclic Ring Structures.

Authors:  Arun K Ghosh; Chad Keyes; Anne M Veitschegger
Journal:  Tetrahedron Lett       Date:  2014-07-23       Impact factor: 2.415

7.  Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations.

Authors:  Ryan J Beattie; Thomas W Hornsby; Gemma Craig; M Carmen Galan; Christine L Willis
Journal:  Chem Sci       Date:  2016-01-11       Impact factor: 9.825

Review 8.  Synthetic efforts on the road to marine natural products bearing 4-O-2,3,4,6-tetrasubstituted THPs: an update.

Authors:  Marta Fariña-Ramos; Celina García; Víctor S Martín; Sergio J Álvarez-Méndez
Journal:  RSC Adv       Date:  2021-02-03       Impact factor: 3.361

9.  Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A.

Authors:  Alba Millán; James R Smith; Jack L-Y Chen; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-14       Impact factor: 15.336
  9 in total

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