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.
2017
80
2384
2388
Scarpi, Dina; Faggi, Cristina; Occhiato, Ernesto G
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1095064
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