Confirmation of the Revised Structure of Samoquasine
A and a Proposed Structural Revision of Cherimoline
Posted on 2018-07-18 - 18:22
The identity of the natural product
samoquasine A has remained
obscure since its isolation from custard apple seeds in 2000. One
of the proposed structures, benzo[f]phthalazin-4(3H)-one, was prepared in two steps by regioselective ortho-lithiation/formylation of N,N-diisopropyl-2-naphthylamide, followed by cyclization
with hydrazine, but was shown to be different from the natural product.
Perlolidine, another candidate structure, was synthesized by a novel
route involving a β-selective Heck reaction of butyl vinyl ether.
Both perlolidine and samoquasine A are converted by trimethylsilyldiazomethane
into the same N-methyl derivative. In addition, the 13C NMR spectra of perlolidine and another structurally mis-assigned
natural product, cherimoline, are almost identical. Thus, both samoquasine
A and cherimoline are actually perlolidine.
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Dhoro, Francis; Parkin-Gibbs, Jesse; McIldowie, Matthew; Skelton, Brian W.; Piggott, Matthew J. (2018). Confirmation of the Revised Structure of Samoquasine
A and a Proposed Structural Revision of Cherimoline. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.8b00319
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AUTHORS (5)
FD
Francis Dhoro
JP
Jesse Parkin-Gibbs
MM
Matthew McIldowie
BS
Brian W. Skelton
MP
Matthew J. Piggott