PMID: 11312933Apr 21, 2001Paper

Synthesis and ring contraction reactions of polyazamacrolides

The Journal of Organic Chemistry
S García-Rubio, J Meinwald

Abstract

The synthesis of three analogues of the single most abundant component of a ladybird beetle (Epilachna borealis) defensive secretion, the trimeric 42-membered polyazamacrolide PAML 681, is described. Construction of the nonnatural macrocyclic trimers began with the preparation of the corresponding monomeric segments, followed by their oligomerization and a final macrolactonization step of the activated linear trimeric hydroxy acid. The relative rates of the O-to-N acyl migrations that are characteristic of PAML 681 itself, as well as of the synthetic analogues, were investigated. These studies showed that changes in the substitution pattern adjacent to the nucleophilic nitrogen atom, along with changes in the size of the oxaazacyclic intermediates, have substantial effects on the polyazamacrolide rearrangement rates.

References

Dec 1, 1968·Proceedings of the National Academy of Sciences of the United States of America·H NeumannA Rich
Jan 3, 1995·Proceedings of the National Academy of Sciences of the United States of America·J Meinwald, T Eisner
Nov 13, 1998·Proceedings of the National Academy of Sciences of the United States of America·F C SchroederJ Meinwald
May 9, 1996·Chemical Reviews·Angela Glisan King, Jerrold Meinwald

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Citations

Oct 26, 2002·Journal of Molecular Graphics & Modelling·Carol ParishMyrianne Dure
Sep 26, 2012·Chemical Reviews·A ParentyJ-M Campagne
May 10, 2012·Journal of Asian Natural Products Research·Qi-Feng ChenFeng-Peng Wang
Mar 11, 2006·The Journal of Organic Chemistry·Mariusz SkwarczynskiYoshiaki Kiso
Mar 9, 2006·Chemical Reviews·A ParentyJ-M Campagne

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