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Asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (−)-nicotlactone B and (−)-galbacin

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Abstract

An efficient asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones from aldehydes and enantioenriched γ-carbamate alkenylboronates is reported. The cornerstone of this strategy is the implementation of sequential [3,3]-allyl cyanate rearrangement/allylboration/nucleophilic addition/cyclisation reactions. Diverse γ-butyrolactones such as the flavouring compounds, (+)-trans-whiskey lactone and (+)-trans-cognac lactone, as well as an advanced intermediate towards the first synthesis of natural products, (−)-nicotlactone B and (−)-galbacin, have thus been obtained.

Graphical abstract: Asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (−)-nicotlactone B and (−)-galbacin

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Publication details

The article was received on 12 Jan 2018, accepted on 08 Feb 2018 and first published on 08 Feb 2018


Article type: Paper
DOI: 10.1039/C8OB00101D
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (−)-nicotlactone B and (−)-galbacin

    S. Henrion, A. Macé, M. M. Vallejos, T. Roisnel, B. Carboni, J. M. Villalgordo and F. Carreaux, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00101D

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