Literature DB >> 10822542

Studies on the synthesis of tedanolide: synthesis of the C(5)-C(21) segment via a highly stereoselective fragment assembly aldol reaction of a chiral beta,gamma-unsaturated methyl ketone.

W R Roush1, G C Lane.   

Abstract

[formula: see text] A highly diastereoselective synthesis of 3, corresponding to the C(5)-C(21) segment of tedanolide, has been accomplished by a route utilizing the aldol reaction of aldehyde 4 and the beta,gamma-unsaturated methyl ketone 5.

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Year:  1999        PMID： 10822542     DOI： 10.1021/ol990572s

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


  3 in total

1.  Total syntheses of (+)-tedanolide and (+)-13-deoxytedanolide.

Authors:  Joshua R Dunetz; Lisa D Julian; Jason S Newcom; William R Roush
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

2.  Diastereoselection in the formation of spirocyclic oxindoles by the intramolecular Heck reaction.

Authors:  Larry E Overman; Donald A Watson
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

3.  A unified approach to the tedanolides: total synthesis of (+)-13-deoxytedanolide.

Authors:  Amos B Smith; Christopher M Adams; Stephanie A Lodise Barbosa; Andrew P Degnan
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-26       Impact factor: 11.205
  3 in total

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