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Synthesis of caeliferins, elicitors of plant immune responses: Accessing lipophilic natural products via cross metathesis

Organic Letters, ISSN: 1523-7060, Vol: 13, Issue: 21, Page: 5900-5903
2011
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Article Description

A cross metathesis (CM)-based synthesis of the caeliferins, a family of sulfooxy fatty acids that elicit plant immune responses, is reported. Unexpectedly, detailed NMR spectroscopic and mass spectrometric analyses of CM reaction mixtures revealed extensive isomerization and homologation of starting materials and products. It is shown that the degree of isomerization and homologation in CM strongly correlates with substrate chain length and lipophilicity. Side-product suppression requires appropriate catalyst selection and use of 1,4-benzoquinone as a hydride scavenger. © 2011 American Chemical Society.

Bibliographic Details

O'Doherty, Inish; Yim, Joshua J; Schmelz, Eric A; Schroeder, Frank C

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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