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Synthesis 2016; 48(14): 2263-2270
DOI: 10.1055/s-0035-1560434
DOI: 10.1055/s-0035-1560434
paper
A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether
Weitere Informationen
Publikationsverlauf
Received: 02. Dezember 2015
Accepted after revision: 29. Februar 2016
Publikationsdatum:
11. April 2016 (online)
Abstract
A strategy toward the biomimetic synthesis of morusalbanol A pentamethyl ether is described. The synthesis is based on a hydrogen-bond-assisted Diels–Alder cycloaddition between a dehydroprenyl diene and a chalcone dienophile. Selective cleavage of the ortho-methyl ether of the resulting cycloadduct allows rotation of the C3–C21 bond and subsequent intramolecular cyclization affords the pentamethyl ether of (±)-morusalbanol A. As with the natural product, morusalbanol A, a number of key proton and carbon signals are absent in the NMR spectra of the title product.
Key words
morusalbanol A - Diels–Alder reaction - mulberry - Morus alba - biomimetic synthesis - natural productsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560434.
- Supporting Information
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