The first total synthesis of the natural product bruceolline I, isolated in small quantities from the ethanol extract of Brucea mollis stems, was achieved in 29% yield over nine steps and with high enantiomeric purity (>98%). The key step of the process is the tandem gold-catalyzed rearrangement/Nazarov reaction of a propargylic acetate derivative. This synthesis provides a sufficient amount of synthesized bruceolline I for further bioassays.
Total Synthesis of Bruceolline I / Scarpi, Dina; Faggi, Cristina; Occhiato, Ernesto G. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 0163-3864. - STAMPA. - 80:(2017), pp. 2384-2388. [10.1021/acs.jnatprod.7b00311]
Total Synthesis of Bruceolline I
SCARPI, DINA;FAGGI, CRISTINA;OCCHIATO, ERNESTO GIOVANNI
2017
Abstract
The first total synthesis of the natural product bruceolline I, isolated in small quantities from the ethanol extract of Brucea mollis stems, was achieved in 29% yield over nine steps and with high enantiomeric purity (>98%). The key step of the process is the tandem gold-catalyzed rearrangement/Nazarov reaction of a propargylic acetate derivative. This synthesis provides a sufficient amount of synthesized bruceolline I for further bioassays.File | Dimensione | Formato | |
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