Journal
ORGANIC LETTERS
Volume 13, Issue 21, Pages 5900-5903Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol202541b
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- National Institutes of Health [GM079571]
- O'Reilly Foundation
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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.
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