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Org Lett. 2011 Nov 4;13(21):5900-3. doi: 10.1021/ol202541b. Epub 2011 Oct 12.

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

Author information

1
Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.

Abstract

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.

PMID:
21992613
PMCID:
PMC3216471
DOI:
10.1021/ol202541b
[Indexed for MEDLINE]
Free PMC Article

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