Total syntheses of (+)- and (−)-syringolides 3 and of (+)- and (−)-syributins 1, 2 and 3

The first total syntheses of (−)-syringolide 3, (+)-syributin 3 and their unnatural enantiomers (+)-syringolide 3 and (−)-syributin 3 using a common intermediate as starting material are described. In addition, total syntheses of (−)- and (+)-syributins 1 and 2 were accomplished by means of the same...

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Bibliographic Details
Published in:Tetrahedron 2009-09, Vol.65 (39), p.8091-8098
Main Authors: Navarro Villalobos, Mauricio, Wood, John L., Jeong, Susan, Benson, Cristy Lindberg, Zeman, Steven M., McCarty, Catherine, Weiss, Matthew M., Salcedo, Analee, Jenkins, Jonathan
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Free radicals chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
O–H insertion
Preparations and properties
Pseudomonas syringae
Reactivity and mechanisms
Rhodium(II) stabilized carbene
Syributins
Syringolides
Total synthesis
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Summary:The first total syntheses of (−)-syringolide 3, (+)-syributin 3 and their unnatural enantiomers (+)-syringolide 3 and (−)-syributin 3 using a common intermediate as starting material are described. In addition, total syntheses of (−)- and (+)-syributins 1 and 2 were accomplished by means of the same methodology. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.07.055