Literature DB >> 15469366

Stereocontrolled construction of either stereoisomer of 12-oxatricyclo[6.3.1.0(2,7)]dodecanes using Prins-pinacol reactions.

Larry E Overman1, Emile J Velthuisen.   

Abstract

[reaction: see text] 12-Oxatricyclo[6.3.1.0(2,7)]dodecanes can be efficiently synthesized in a stereoselective manner by Prins-pinacol reactions. By biasing the transition state of the Prins cyclization, it is possible to access either stereoisomer of this oxatricyclic ring system.

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Year:  2004        PMID： 15469366     DOI： 10.1021/ol0482745

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


  4 in total

1.  Molecular Rearrangements in the Construction of Complex Molecules.

Authors:  Larry E Overman
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

2.  Identification of an Unexpected 2-Oxonia[3,3]sigmatropic Rearrangement/Aldol Pathway in the Formation of Oxacyclic Rings. Total Synthesis of (+)-Aspergillin PZ.

Authors:  Stephen M Canham; Larry E Overman; Paul S Tanis
Journal:  Tetrahedron       Date:  2011-09-19       Impact factor: 2.457

3.  Origin of stereocontrol in the construction of the 12-oxatricyclo[6.3.1.0(2,7)]dodecane ring system by Prins-pinacol reactions.

Authors:  Larry E Overman; Paul S Tanis
Journal:  J Org Chem       Date:  2010-01-15       Impact factor: 4.354

4.  Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.

Authors:  Zhi-Wei Jiao; Yong-Qiang Tu; Qing Zhang; Wen-Xing Liu; Shu-Yu Zhang; Shao-Hua Wang; Fu-Min Zhang; Sen Jiang
Journal:  Nat Commun       Date:  2015-06-17       Impact factor: 14.919
  4 in total

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